The Best Fall Road Trips in the Midwest

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The best fall road trips in the Midwest will take you through northern Minnesota, coastal Michigan, eastern Wisconsin, central Indiana, and even a portion of the Great River Road alongside the Mississippi River.
Autumn is a wonderful time to explore the Midwest. With beautiful fall colors and lots of regional festivals and traditions, you can’t go wrong when it comes to choosing the best fall road trips in the Midwest.
Here is just a sampling of five great road trips, perfect for romantic getaways, family Halloween celebrations, or food and wine sampling tours.
But before you hit the road, download the free insurance comparison app Jerry and check out the roadside assistance program. It features jump starts, tire changes, lockout assistance, and more so that you can enjoy the scenery worry-free.
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North Shore Scenic Byway—Key trip details

Duluth to Grand Marais, MN
Duluth to Grand Marais, MN
The North Shore Scenic Byway is a popular drive at any time of year, but especially in the fall, when the leaves change color. The inland maple trees are the first to change, with brilliant reds and golds, while the aspens and birch trees peak a couple of weeks later with bright yellow leaves.
Follow this route for gorgeous views of Lake Superior, plenty of outdoor activity, and access to all that Minnesota has to offer along its lighthouse-dotted shoreline.
Total distance (round-trip): 290 miles
Total driving time (round-trip): 5 hours, 20 mins
Total time needed: 4 to 7 days
Fall color peak: Mid-September to early October inland, late September to mid-October on the shoreline


  • Duluth, MN—1 to 2 days
  • Lutsen, MN—1 to 2 days
  • Grand Marais, MN—1 to 2 days

Start in Duluth, MN

With family activities, lots of green spaces, and autumnal flavors, Duluth is the perfect place to begin your fall road trip in Minnesota.

Where to stay in Duluth

  • The Inn on Lake Superior—If you’re not a local, rest your head at The Inn on Lake Superior. The Inn is right on Lake Superior and is less than a mile from the Aerial Lift Bridge, and it offers amenities like a fitness center and pools. Cost per night: from $112

What to do in Duluth

Lift Bridge in Duluth seen from across a both of water.
Lift Bridge, Duluth
  • Lake Superior Marine Museum—Come to this engaging museum to learn about the history of the Great Lakes and the inner workings of Minnesota’s shipping industry. From here, you’ll also have a great view of Duluth’s iconic Aerial Lift Bridge in the harbor.
  • Spirit Mountain ($$)—Visit the Adventure Park at Spirit Mountain for beautiful views mixed with some adrenaline. Here, you can fly down the mountain on the Timber Twister alpine roller coaster or the Timber Flyer zip ride. There’s also a scenic chairlift if you want to take in the fall foliage at lower speeds.
  • Scarium at the Aquarium ($$) or Boo at the Zoo ($$)—If you have little ones and you’re in town in late October, you can take the kids trick-or-treating at Scarium at the Aquarium or Boo at the Zoo (we love a good rhyme!). Of course, both destinations are still worthwhile without the costumes.
  • Stroll along The Lakewalk for a beautiful view of Lake Superior and access to several city parks and other tourist destinations.
  • Glensheen Mansion ($$)—Take a tour of the historic Glensheen Mountain. This sprawling property has beautiful gardens and a house with 39 rooms, and you’ll learn all about the history of Duluth while you’re there.

Where to eat and drink in Duluth

  • Duluth Grill ($$)—Grab a bite at Duluth Grill, a cozy, family-owned diner serving local and organic food that won’t disappoint. Try the Apple Crisp Waffle for a real treat.
  • Wild State Cider ($$)—Toast the start of your road trip with seasonal beverages like apple pie cider at Wild State Cider. All of their ciders are made in-house, featuring natural ingredients free from added chemicals.
  • Camp Creemee ($)—Conjure up fall in New England with maple syrup soft-serve at Camp Creemee, a Vermont-style ice cream shop conveniently located inside of Wild State Cider.
Pro Tip On your way out of town, go bird watching at the Hawk Ridge Nature Preserve, just off Skyline Parkway. From mid-September to late October, you can witness the magnificent fall migration of hawks and eagles from this overlook.

Duluth to Lutsen

92.1 miles, 1 hour 40 minutes
From MN-61 in Duluth, take a detour at Brighton Beach to Scenic 61 (Congdon Blvd), heading north. This offshoot from the highway hugs the shoreline, giving you beautiful lake views as you wind your way through several quaint towns. Merge back onto the highway at Sannes Road after Larsmont.
On your drive, wave to the Pierre the Voyageur statue—this giant, pantless French man holds a canoe paddle next to the highway in Two Harbors. If that sentence stopped you in your tracks, pull over and take a picture with him.

Where to see the best leaves from Duluth to Lutsen

Waterfall with fall trees in the background at Gooseberry Falls State Park, Lutsen.
Gooseberry Falls State Park, Lutsen
  • Gooseberry Falls State Park—See a series of waterfalls and amble through aspen, cedar, pine, and spruce forests.
  • Iona’s Beach—Stop here for views of fall colors and to walk along the unique pink rocks that make up the beach. If you’re quiet, you might be able to hear the bell-like sound made by the waves moving the rocks around.
  • Split Rock Lighthouse—This is one of the most picturesque lighthouses in the country, especially in the fall. Tour guides dress up in costumes from the 1920s while they teach you about lightkeeper life.

Where to stay in Lutsen

  • Caribou Highlands Lodge—This comfortable lodge is right in Lutsen and nestled into the Sawtooth Mountains, making it a great place to stay, relax, and enjoy the fall scenery. Cost per night: from $151
  • Illgen Falls Cabins—If you want to break up this leg of the journey, you can make your home base in one of the small towns near Tettegouche State Park. These cabins are a convenient option for those who want to spend more time outdoors. Cost per night: from $220

What to do in Lutsen

  • Temperance River State Park—The state park is right in Lutsen and offers tremendous opportunities to walk along the river gorge, see waterfalls, and marvel at the fall colors.
  • Superior Hiking Trail—Hike a portion of the Superior Hiking Trail. This trail has many access points throughout your road trip, but this portion of the trail can get you to Carlton Peak. It’s three miles round trip from the Britton Peak Trailhead, and you’ll be rewarded with top-of-the-world views.
  • Summit Express Gondola—Ride the gondola to the top of Moose Mountain for gorgeous views of the fall foliage and Lake Superior. You can eat lunch at the Summit Chalet if you’re not ready to go back down.
  • Oberg Mountain—Hike Oberg Mountain, one of the most popular trails in the region, for spectacular views of the maple trees.

Where to eat and drink in Lutsen

  • North Shore Winery ($$)—Reward yourself for all that hiking with a visit to the North Shore Winery. Try some of their award-winning wines and ciders that highlight local flavors.
  • Cascade Restaurant & Pub ($$)—This is the place to go for a hearty meal. Fill up with their grain bowls or flatbreads before you head out on your next trek.

Lutsen to Grand Marais

17.8 miles, 20 minutes
Named “America’s Coolest Small Town,” Grand Marais has plenty to offer visitors of the North Shore.
From Lutsen, get back on MN-61 north to Grand Marais.

Where to stay in Grand Marais

  • Naniboujou Lodge—Spend the night at this colorful Art Deco hotel with a storied history. There’s easy access to hiking trails, so you’re never too far away from fall tranquility. Cost per night: from $299

What to do in Grand Marais

White water falling over rocks as seen through fall trees at Sable Falls, Grand Marais.
Sable Falls, Grand Marais
  • North House Folk School—Visit this classic folk school, and take a class on Scandinavian painting, basket-making, or blacksmithing. In late October, they offer programming geared towards families, like woodworking classes for kids.
  • Devil’s Kettle Falls—Marvel at the mysterious Devil’s Kettle Falls in Magney State Park, where the river splits in two. Half of the water flows down a waterfall and continues downstream, while the other half confounds visitors by disappearing into a pothole, never to reemerge.

Where to eat and drink in Grand Marais

  • Angry Trout Cafe ($$)—Order the fresh Lake Superior fish of the day at one of the most popular eateries in town.
  • Naniboujou Lodge Restaurant ($$)—Enjoy delicious food and a spectacular dining room at the Naniboujou Lodge Restaurant, even if you’re not staying at the Lodge. The colorful decor will blow you away.
Pro Tip Drive up to the Canadian border to see the very end of the Scenic Byway. Learn about the history of the North American fur trade at the Grand Portage National Monument, then marvel at Minnesota’s tallest waterfall in Grand Portage State Park.

Driving home

Lucky for you, the scenic route is also the fastest route back to Duluth from Grand Marais. Take MN-61 the whole way.
If you want to extend your trip, consider stopping in some of the small towns you passed over, like Silver Bay, Finland, and Tofte.
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M-22 Color Tour—Key Trip Details

M-22 Road Trip
M-22 From Manistee to Traverse City
The M-22 in Michigan was practically designed for lovers of fall color.
Hugging Lake Michigan, this road winds around the Leelanau Peninsula from Manistee to Traverse City. Along the way, you’ll have breathtaking views of the lake, access to incredible wineries, and an opportunity to experience the one-of-a-kind Sleeping Bear National Lakeshore.
Total distance (round trip): 116 miles
Total driving time (round trip): 2 hours, 40 minutes
Total time needed: 3 to 5 days
Fall color peak: Mid-October

M-22 Color Tour Itinerary

  • Manistee, MI—1 day
  • Frankfort, MI—One half to 1 day
  • Glen Arbor, MI—1 day
  • Traverse City, MI—1 to 2 days

Start in Manistee

The M-22 kicks off in this quaint Victorian town full of historic buildings and charm.
If you’re driving here from Grand Rapids or Detroit, take I-96 west to US-31 north. Take exit 170A, then head north on Stiles Road, Quarterline Road, and Maple Road, until you reach Manistee.

Where to stay in Manistee

  • The Dempsey Manor B&B—If you’ve never spent the night in a Victorian mansion, you’ll have your chance at The Dempsey Manor. This picturesque B&B is perfectly situated on the coastline, so you can relax and enjoy the Victorian charm. Cost per night: from $149
  • Manistee Hotel—Manistee Hotel provides travelers with more typical accommodations. The no-frills hotel is an easy spot to stay overnight, and it is close to many popular attractions.

What to do in Manistee

A wooden fence in the woods over an overlook at Manistee River Highbanks, Manistee.
Manistee River Highbanks, Manistee
  • Downtown Manistee—Stroll through the historic downtown, which is full of Victorian buildings and cute shops.
  • Tunnel of Trees—This isn’t marked on a map, but this drive is magical. It starts at the intersection of M-55 and Main Street.
  • Lake Bluff Arboretum—Check out the Michigan Champion Giant Sequoia at the Lake Bluff Arboretum. You don’t often see sequoias outside of California, but there are three at this arboretum, brought over from California as seedlings in 1948.

Where to eat in Manistee

  • Blue Fish Kitchen & Bar ($$$)—For fish from the Great Lakes and other local fare, visit the Blue Fish Kitchen & Bar. Though there are other proteins on the menu, the locally-caught Walleye is not to be missed.

Manistee to Frankfort

35.2 miles, 47 minutes
Frankfort, MI is a nature-lovers paradise, with pristine shores, gorgeous dunes, and incredible sunsets sure to delight every visitor.
Take US-31 north to M-22. Along the way, pull over at the Arcadia Scenic Lookout and climb the stairs for a great view of Lake Michigan.

Where to stay in Frankfort

  • Hotel Frankfort—Though you may not decide to stay here for a night, the historic Hotel Frankfort offers lovely accommodations, with themed rooms and easy access to the beach. (Cost per night: from $100)

What to do in Frankfort

A stormy view of a white lighthouse with a red roof and an American flag nearby.
Point Betsie Lighthouse, Frankfort
  • Point Betsie Lighthouse—Explore the photogenic Point Betsie Lighthouse. If you really love it here, you can try to book a stay in the Keeper’s Quarters. Reservations go fast, so keep an eye on the website.
  • Frankfort Beach—Take some time to relax on Frankfort’s lovely beach. It’s the perfect place to enjoy the crisp fall air with a book.

Where to eat in Frankfort

  • Stormcloud Brewing Company ($$)—Try a Belgian-inspired beer at Stormcloud Brewing Company. The casual spot is also known for its flatbread pizza and meat, cheese, and pickle plates.
  • Crescent Bakery ($$)—For a quick breakfast, grab a fresh pastry at Crescent Bakery.

Frankfort to Glen Arbor

29.8 miles, 41 minutes
Hop back on the M-22 and head over to the charming town of Glen Arbor, which was named one of the “Most Beautiful Places in America”.
Along the way, you’ll drive right over Platte River, where hundreds of salmon swim upstream every fall to spawn. See if you can catch a peek. You can also take a driving break to hike the Empire Bluff Trail through beech and maple trees until you reach the bluff at the top—which has killer views of fall foliage and the lake.

Where to stay in Glen Arbor

  • The Homestead Resort—Stay right in the middle of the dunes at this scenic resort. The resort consists of a few hotels, each with amenities to make a family vacation fun and relaxing. Cost per night: from $350

What to do in Glen Arbor

An expanse of sand on the left slants down toward some blue lake water.
Sleeping Bear Dunes National Lakeshore, Glen Arbor
  • Sleeping Bear Dunes National Lakeshore—Besides the spectacular views along M-22, your visit to the Sleeping Bear Dunes National Lakeshore might just be the highlight of your trip. This area feels like it’s still untouched by man, and you could spend days exploring the sandy beaches, bluffs, forests, and lakes.
  • Pierce Stocking Scenic Drive—If you’re looking to stay in your car, take the Pierce Stocking Scenic Drive, a magnificent 7.4-mile loop with prime views of the dunes.

Where to eat and drink in Glen Arbor

  • Leelanau Peninsula Wine Trail—The Leelanau Peninsula Wine Trail organizes vineyard tours around Michigan’s wine regions. In October, you can partake in “The Hunt for the Reds of October” wine tasting tour.

Glen Arbor to Traverse City

40.3 miles, 57 minutes
Known as the cherry capital of the world, Traverse City is a great destination for local produce, world-class wineries, and relaxing beaches.
Back on the M-22, this last stretch will guide you up and around the Leelanau Peninsula and through many picturesque northern Michigan towns. Ultimately, the road will end in Traverse City.

Where to stay in Traverse City

  • The Beach Haus Resort—This gorgeous resort is the perfect place to relax for a few days after your drive. With a beachside backyard and recreational activities (bocce ball, anyone?), it’s a great spot for a family vacation. Cost per night: from $71

What to do in Traverse City

Two skaters stand in front of a marquee that announces the Traverse City film festival.
Downtown Traverse City
  • Cherry Republic—Visit Cherry Republic for cherry-flavored everything, from jams and pies to hot sauce and mustard. Think of something edible, and they’ll add cherries.
  • Go to a pumpkin patch or corn maze—Throughout the fall, you can find fun destinations for the whole family in Traverse City, like corn mazes and pumpkin patches. They also have plenty of wine and beer tastings, if you want to leave the kids at home.

Where to eat in Traverse City

  • Apache Trout Grill ($$) Pay homage to the region’s rich fishing history at the Apache Trout Grill and order some of their famous fresh fish—the Apache whitefish is a favorite.
  • Trattoria Stella ($$$)—Indulge in upscale Italian fare at Trattoria Stella, known for their house-made pasta.

Driving home

To get to Grand Rapids, you’ll take Garfield Road south then head east on M-113. Once it merges with US-131, you’ll continue south to Grand Rapids.
To get to Detroit, you’ll take M-72 east and then I-75 south.
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Eastern Wisconsin: Chicago, IL to Door County, WI—Key trip details

Road trip map from Chicago, IL to Door County, WI
Chicago, IL to Door County, WI
This road trip will take you from Illinois to two of the most beautiful vacation destinations in Wisconsin. Along the way, you’ll get to enjoy lots of regional history, partake in Halloween activities, and of course, bask in the stunning fall colors that surround you.
Total distance: 591 miles
Total driving time: 9 hours, 51 minutes
Total time needed: 4 to 7 days
Fall color peak: Mid-October

Eastern Wisconsin itinerary

  • Chicago, IL—2 to 3 days
  • Lake Geneva, WI—1 to 2 days
  • Door County, WI—1 to 2 days

Start in Chicago

You can’t cover everything Chicago has to offer in just one day. But to break it down a little, you can focus on Halloween-themed events and outdoor activities, where you can see Chicago’s incredible architecture, framed by the city’s fall colors.

Where to stay in Chicago

  • Hotel Versey—The Hotel Versey is an ideal location near the Lincoln Park Zoo. The boutique hotel captures the best of hip, urban Chicago and combines it with the historic tradition of the city. Cost per night: from $88
  • Swissotel Chicago—For swankier accommodations, the Swissotel Hotel will give you a view of Lake Michigan and the Chicago River. Cost per night: from $91

What to do in Chicago

The Chicago skyline in fall as seen from across a pond in Lincoln Park.
Lincoln Park, Chicago
  • Lincoln Park— Lincoln Park is a great place to see colorful fall foliage. While you’re there bring the family to Fall Fest at the Lincoln Park Zoo, where you can snack on festive food, get a Halloween-themed face painting, and watch professional pumpkin carvers at work.
  • Halloween ghost tour—Take a tour through Chicago, and learn some spine-chilling secrets about the city you thought you knew.
  • Chicago Architecture Biennial—For less terrifying diversions, go on a walking tour of the many free exhibits at the annual Chicago Architecture Biennial.

Where to eat in Chicago

  • The Publican ($$$)—Try the The Publican ($$$) for an eclectic menu and a communal feel in the dining room. The restaurant is known for its oysters, pork dishes, and beer, so you won’t want to miss those specialties.
  • Pequod’s Pizzeria ($$)—If you came to Chicago for deep-dish pizza, Pequod’s Pizzeria is the place for you.

Chicago to Lake Geneva

83 miles, 2 hours
A popular summer resort destination, Lake Geneva is also a great place for an autumnal getaway because of its colorful fall foliage, historical architecture, and beautiful setting.
On your drive, stop and pick some apples at Goebbert’s Farm and Apple Orchard. They also have a pumpkin patch, but you might want to save that activity for the return trip—pumpkins don’t travel as well as people do.
To get to Lake Geneva, take I-90 west to IL-47 north.

Where to stay in Lake Geneva

  • The Abbey Resort—The Abbey is a full-service resort on Lake Geneva. If you book a room here, you can indulge in the onsite dining and Immersion Cinema. There’s even kids’ programming if you need a break from the family. Cost per night: from $120
  • Maxwell Mansion—For a slightly more unique experience, spend the night at the Maxwell Mansion. As the first mansion built in Geneva (it’s been here since 1856!), the six-room mansion offers guests a luxurious stay for ultimate relaxation. Cost per night: from $200

What to do in Lake Geneva

A white mailbox stands on the left side of a road covered with orange fall trees.
A rustic road in Lake Geneva
  • Lake Geneva Boat Tours Get a unique view of the lake with one of the area’s very popular boat tours.
  • Walk the Shore Path— Along the famous Shore Path, you’ll get a tour of the area’s incredible Gilded Age mansions, originally built as luxury retreats for Chicago’s elite. The entire path is 26 miles, so you might want to choose a portion of it that seems the most appealing.
  • Black Point Estate and Gardens ($$$)—Tour the rooms and grounds of this incredible mansion built in 1888. Though tickets are pricey, your ticket includes entrance to the Victorian Mansion, Estate and Gardens, and a 45-minute boat ride.
  • Dan Patch Stables ($$)—Take a trail ride with Dan Patch Stables for a scenic tour of the area.

Where to eat in Lake Geneva

  • Egg Harbor Cafe ($$)—For a seasonal treat, indulge in the pumpkin pancakes at this popular brunch spot.
  • Sopra Bistro ($$$)—Sopra features a seasonably-inspired menu of Italian classics with a twist, like rich seafood pasta or grilled pork with a whiskey-sage sauce.

Lake Geneva to Door County

207 miles, 3 hours 8 minutes
Autumn is a wonderful time to visit Door County because of the brilliant fall colors. Many people find Door County to be more reminiscent of New England, but you’ll definitely find the signature charm and hospitality of the Midwest in these delightful small towns.
Take US-12 west, then I-43 north to Green Bay. Get on the WI-57 north to Door County.

Where to stay in Door County

  • Bridgeport Waterfront Resort—For accommodations at the gateway to the peninsula, stay at this lovely resort in Sturgeon Bay. Cost per night: from $137
  • The Blacksmith Inn on the Shore—Further down the peninsula, you could book a room at The Blacksmith Inn on the Shore in Baileys Harbor. This tranquil B&B is a great accommodation for days when you want to revel in some peace and quiet. Cost per night: from $145

What to do in Door County

A small yellow house with a red lighthouse tower sits in a park with fall leaves in Door County.
Eagle Bluff Lighthouse, Door County
  • Drive the Peninsula—The best way to see Door County is by driving a loop around the peninsula, starting and ending in Sturgeon Bay.
  • Cave Point County Park—Visit Cave Point County Park to marvel at the dramatic carved rock faces.
  • Popelka Trenchard Glass—Take a class or watch a public demonstration at Popelka Trenchard Glass, a hot glass studio.
  • Door County Wine Trail—Take an educational tour to learn about the agriculture and wine production in this region, and—of course—taste some unique, regional wine.

Where to eat in Door County

  • Sweetie Pies ($$)—Pick up a delicious homemade pie at Sweetie Pies in Fish Creek. Some favorites include chocolate chip walnut, apple-cherry, and Packer pie.
  • Old Post Office Restaurant ($$)—Attend an old-fashioned fish boil at the Old Post Office Restaurant in Ephraim—yes, it’s actually in an old post office!

Driving home

From Sturgeon Bay, take I-43 south, then I-94 east to Chicago. You’ll pass right through Green Bay and Milwaukee, in case you want to prolong your trip.
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Central Indiana: Indianapolis to Parke County—Key trip details

Indianapolis to Parke County road trip map.
Indianapolis to Parke County, IN
Explore some of Indiana ‘s hidden gems on this road trip that takes you through a mecca of modern architecture, a vibrant artist’s colony, a selection of quirky fall festivals, and the largest concentration of covered bridges in the world—all while enjoying the state’s magnificent fall foliage.
Total distance: 214 to 278 miles
Total driving time: 4 hours, 43 minutes to 6 hours, 30 minutes
Total time needed: 4 to 7 days
Fall color peak: Mid-October

Central Indiana itinerary

  • Indianapolis, IN—1 to 2 days
  • Columbus, IN—One half day
  • Nashville, IN—1 to 2 days
  • Bloomington, IN—1 to 2 days
  • Parke County, IN—1 to 2 days

Start in Indianapolis

Indianapolis is bustling with fall events to get you in the mood for this road trip. You can explore the city’s art, cuisine, and outdoor spaces on this first leg of the trip.

Where to stay in Indianapolis

  • OMNI Severin Hotel—The Omni Severin is centrally located and has luxury hotel amenities for a comfortable stay. Cost per night: from $138
  • Bottleworks Hotel—If you’ve always wanted to stay in the former Coca-Cola Bottling Company building, now’s your chance. The Bottleworks Hotel combines history, modern luxury, and a bit of whimsy for a unique experience. Cost per night: from $219

What to do in Indianapolis

The Indianapolis skyline, seen from across the canal, partially obscured by fall trees.
Canal walk, Indianapolis
  • Harvest at Newfields—Get into the fall spirit with this annual festival. Throughout October, you can walk through glowing pumpkin paths at night or enjoy food and drinks from local vendors during the day. It’s a highly anticipated event for the whole family.
  • Indianapolis Museum of Art—The Indianapolis Museum of Art is a part of Newfields Indianapolis. The museum features works from some of the world’s most famous artists, including Rembrandt, O’Keefe, and Picasso, along with artwork from around the world.
  • Fort Benjamin Harrison State Park—Fort Benjamin Harrison State Park has some of the best spots for fall foliage in the city. Take a stroll in the park for a quiet respite from downtown.

Where to eat and drink in Indianapolis

  • Sangiovese Ristorante ($$)—Enjoy an intimate dinner at this local favorite. The menu features classics like lasagna alla bolognese and scallopini alla piccata for an authentic Italian meal.
  • Cake Bake Shop ($)—Try seasonal dessert, like pumpkin ginger cake or southern-style caramel cake at this hometown bakery.

Indianapolis to Columbus

46.2 miles, 50 minutes
Columbus is a bit of a hidden gem in Indiana. In 1957, the CEO of Cummins established a foundation and offered to pay all of the fees for any architect to create a new public building in Columbus. As a result, this small city became a surprising center for modern architecture, with buildings by I.M. Pei, Eero Saarinen, and Richard Meier, among others.
From Indianapolis, take I-65 south, then IN-46 east to Columbus.

What to do in Columbus

  • Go on a walking tour—Explore some of the most notable modernist buildings in the city, including First Baptist Church, Irwin Union Bank, First Christian Church, Cleo Rogers Memorial Library, and the Miller House.
  • Exhibit Columbus—Through November, you can see design-related exhibits and presentations at the annual festival.

Columbus to Nashville

18.5 miles, 25 minutes
Nashville—Indiana, that is, not Tennessee—is the seat of Brown County, which is renowned for its fall foliage and pleasant autumnal drives. For more than 100 years, artists have flocked to Brown County for its beautiful colors and inspirational vistas. Today, Nashville is still a vibrant artists colony with unique shops, art galleries, and charming B&Bs.
Take State Road 46 west from Columbus towards Nashville.

Where to stay in Nashville

  • Robinwood Inn—Rent a charming cabin at the Robinwood Inn for a rustic getaway in the woods of Brown County. Cost per night: from $175
  • Artists Colony Inn—Near downtown Nashville, the Artists Colony Inn used to be an artists’ retreat. Today, it’s a lovely inn close to the many shops and restaurants in the town. Cost per night: from $120

What to do in Nashville

Fall trees seen from across a body of deep blue water in Brown County State Park, Nashville, IN.
Brown County State Park, Nashville, IN
  • Rent a kayak—Explore the lakes of Yellowwood State Forest by boat!
  • Brown County State Park—Go hiking, mountain biking, or horseback riding through Brown County State Park. It’s a great way to see the beautiful changing leaves in this area.
  • T.C. Steele State Historic Site—Tour the estate that inspired iconic Indiana impressionist artist T.C. Steele. The site is the artist’s former home and studio, and it currently displays over 50 works of art.

Where to eat in Nashville

  • Nashville General Store and Bakery—It’s hard to resist the smell of fresh-baked bread at this popular bakery. Stop by for breakfast or grab a sandwich to take with you on the road.
  • Bear Wallow Distillery—Try handcrafted whiskey at the Bear Wallow Distillery located in nearby Gnaw Bone. The distillery only uses locally-grown grains, so the tastes are unique to the region.

Nashville to Bloomington

18.5 miles, 30 minutes
As the home of Indiana University (IU), Bloomington is always bustling with students, college traditions, and community events.
Continue on State Road 46 west from Nashville to Bloomington.

Where to stay in Bloomington

  • Grant Street Inn—Take your pick of 40 unique rooms at this charming boutique inn. A hearty breakfast buffet is included with your stay. Cost per night: from $104
  • Century Suites—For a lovely hotel with beautifully landscaped gardens, the Century Suites are a lovely, relaxing option. Cost per night: from $115

What to do in Bloomington

Indiana University football players in red and white uniform run onto a football field.
Indiana University football
  • IU Football—Cheer on the Hoosiers at an IU football game as fall football season gets underway.
  • Dunn’s Woods—Watch the leaves change on a stroll through this scenic part of the IU campus.
  • Great Glass Pumpkin Patch—If you are in Bloomington in October, you can marvel at the incredible blown-glass pumpkins on display at the annual Great Glass Pumpkin Patch festival.

Where to eat in Bloomington

  • Oliver Winery—For wine you won’t try anywhere else, head to Oliver Winery to try the apple pie wine.
  • Scenic View Restaurant ($$)—The name speaks for itself. Enjoy dinner and a view over Monroe Lake while you dine on the eatery’s upscale, American fare.

Bloomington to Parke County

63.1 miles, 1 hour 30 minutes Parke County is considered the “Covered Bridge Capital of the World” because of its 31 historic covered bridges. These covered bridges, set against the stunning backdrop of the Indiana foliage, make for a very scenic fall drive.
From Bloomington, take State Road 46 west to IN-59 north and head into Parke County.

Where to stay in Parke County

  • Turkey Run Inn & Cabins—These cabins are right in the middle of Turkey Run State Park if you’re looking for a scenic and quiet stay out in nature. Cost per night: from $116
  • Granny’s Farmhouse B&B—Spend a quaint night on this farm in Marshall. This lovely farmhouse has been a landmark site in Park County for over a century! Cost per night: from $120

What to do in Parke County

A red covered bridge in Parke County sits over a small waterfall with a mill beside it.
A covered bridge in Parke County
  • Parke County Covered Bridge Festival—This is the biggest attraction in the region, and it happens every October. For these ten days, your driving tour will be even more worthwhile, since the region’s towns each offer crafts, food, and activities for the whole family.

Where to eat in Parke County

  • Thirty-Six Saloon ($$)—Enjoy a casual meal either inside or on the outdoor “Hog Pit” deck. This relaxed saloon serves American comfort food classics and mouth-watering barbecue.
  • WheelHouse Donuts ($$)—On your way out of town, grab a Fruity Pebbles donut (or one of many other unusual flavors) at WheelHouse Donuts.
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Great River Road: Minneapolis, MN to Dubuque, IA—Key trip details

Great River Road
Great River Road from Minneapolis, MN to Dubuque, IA
Many consider the Great River Road to be the ultimate American road trip. Running from Minnesota to Louisiana, this path follows the Mississippi River through 10 states.
The Wisconsin portion makes for a fantastic fall road trip, with beautiful fall colors, seasonal cuisine, and even a stop at Oktoberfest.
Total distance (round-trip): 533 miles
Total driving time (round-trip): 10 hours, 17 minutes
Total time needed: 4 to 7 days
Fall color peak: Early to mid-October

Great River Road itinerary

  • Minneapolis, MN—2 to 3 days
  • La Crosse, WI—1 to 2 days
  • Dubuque, IA—1 to 2 days

Start in Minneapolis

You could easily spend weeks in Minneapolis, exploring its many city parks and cultural centers, while enjoying the friendly atmosphere. But for now, it’s just the starting point of your road trip.

Where to stay in Minneapolis

  • The Chambers Hotel—Conveniently located in Minneapolis’s famed theatre district, the Chambers Hotel offers some of the best views of the city and easy access to top attractions. Cost per night: from $179
  • Nicollet Island Inn—If you want to get as close as possible to the water, spend the night here—located literally in the middle of the Mississippi River. Cost per night: from $249

What to do in Minneapolis

A waterfall seen through green trees at Minnehaha Park, Minneapolis.
Minnehaha Park, Minneapolis
  • Grand Rounds National Scenic Byway—Take a self-guided tour of Minneapolis by driving portions of this scenic route.
  • Minnehaha Park—The impressive park is worth exploring, especially the 53-foot *Minnehaha Falls and the Pergola Gardens.
  • Minnesota Zoo Jack-O-Lantern Spectacular—Throughout October, take the kids to the zoo to see thousands of jack-o-lanterns lit up at night.

Where to eat in Minneapolis

  • Minneapolis Cider Co ($)—The locally-owned cider company features craft ciders, one-of-a-kind cocktails, and authentic French crepes and galettes. Oh, and you can also play pickleball.
  • FIKA Cafe ($$)—Get a Swedish pastry for breakfast from FIKA Cafe before you hit the road.

Minneapolis to La Crosse

158 miles, 2 hours 30 minutes
La Crosse is a college town full of fall fun, especially in October, when over 100,000 people arrive for the city’s renowned Oktoberfest celebration.
Follow US-10 east to WI-35 south. Take US-53 south to La Crosse.

Where to stop between Minneapolis and La Crosse

  • Stockholm Pie and General Store ($$)—Grab a slice of seasonal pumpkin-pecan pie and fuel up for your journey.
  • Buena Vista Park Overlook—Hike up to this overlook in Alma for stunning views of the Mississippi and epic fall leaves.

Where to stay in La Crosse

  • The Charmant Hotel—Conveniently located in downtown La Crosse, the Charmant Hotel is the only boutique hotel in the city. The establishment partners with local vendors to provide some of the most unique experiences in La Crosse. Cost per night: from $125

What to do in La Crosse

A panoramic view of Grandad Bluff, La Crosse and green trees below.
Grandad Bluff, La Crosse
  • Oktoberfest—La Crosse has the longest-running Oktoberfest in the Midwest. For one weekend at the beginning of October, you can enjoy stein races, barrel rolls, polka dancing, and of course, lots and lots of beer.
  • La Crosse Queen—Get out on the water and take a paddlewheel cruise on the Mississippi.
  • Visit Grandad Bluff—With far-reaching views of Wisconsin, Minnesota, and Iowa, you can basically see your entire road trip route from up here!

Where to eat in La Crosse

  • 4 Sisters ($$)—With a great location across from Riverside Park, visit 4 Sisters for delicious small plates, tapas, and wine.
  • The Pearl ($)—For dessert, get a scoop of old-fashioned, homemade ice cream at this old-timey ice cream and candy shop.

La Crosse to Dubuque

117 miles, 2 hours 30 minutes
Dubuque is Iowa’s oldest city, and it has a long industrial history to prove it. Nowadays, its reinvigorated downtown, green spaces, and art scene have earned it the nickname “Masterpiece on the Mississippi.”
Follow the Great River Road route south along WI-35 to County Road C in Wyalusing. Take WI-133 south to Highway 61. Continue on Highway 61 across the river to Iowa.

Where to stay in Dubuque

  • Grand Harbor Resort and Waterpark—Perfectly located on the Dubuque Harbor, the resort is fun for the whole family—complete with an indoor/outdoor waterpark, arcade, and laser maze.
  • Black Horse Inn—If you’re looking for quieter lodgings, try the Black Horse Inn, a small B&B with four spacious suites.

What to do in Dubuque

The gold tower of the Dubuque County Courthouse on a cloudy day.
The Dubuque County Courthouse
  • Mississippi River Museum and Aquarium—If you want to learn more about the river you’ve been following throughout this trip, check out the exhibits at the Mississippi River Museum and Aquarium.
  • Schuster’s Pumpkin Patch—Open in October, stop here to pick up a pumpkin to take home with you.
  • Fenelon Place Elevator—Take in the views of Dubuque from the Fenelon Place Elevator, a funicular railway that will give you great views of Iowa’s fall foliage.

Where to eat in Dubuque

  • Brazen Open Kitchen Bar ($$$)—If you’ve never heard of “scratch cooking”, immerse yourself in this philosophy at Brazen Open Kitchen, where you can indulge in small-batch meals made with local ingredients.
Pro Tip For the scenic route, you can retrace your steps along the Great River Road or switch over to the Iowa/Minnesota side of the Mississippi. For a more direct shot back to Minneapolis, take IA-3 west to US-52 north.

Why you need roadside assistance

Now that you’re prepared for your fall road trip, it’s time to make sure that you—and your car—are ready for the long drive.
In addition to having ample car insurance, prepare by getting roadside assistance.
Jerry’s roadside assistance program can help you with any emergency services you may need during your road trip, like vehicle towing, fuel delivery, or rental vehicle roadside reimbursement—and it’s only $6.99 per month for one car!

Finding cheap car insurance

Jerry can also help you find the lowest rates on your car insurance by compiling competitive quotes from insurance providers so that you don’t have to spend your time comparison shopping for the best rates.
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