Heading South on a Road Trip from NYC to Nashville

Find out if you’re getting ripped off on your car insurance in less than two minutes.
No long forms · No spam · No fees
From the lights of New York City to artsy Harrisburg, the Shenandoah Valley to the Blue Ridge Mountains, this road trip takes you through some beautiful natural and historical sites on your way to Music City.
Major cities like New York and Nashville always attract tourists and locals alike—but the journey may even be more fun than the destination! This 14-hour drive can be broken up into smaller legs that you can enjoy over the course of four or five days as you head from the big city into the south.
Pack up the car, grab some friends, and gather all the snacks. But don’t even think about hitting the road without the right car insurance and a great roadside assistance plan! Jerry’s roadside assistance gives you peace of mind no matter where you are, with 10 miles of towing, vehicle jumpstarts, fuel delivery, and more—all for just $6.99.
All ready? Time to hit the road!
Compare auto insurance policies
No spam or unwanted phone calls · No long forms · No fees, ever

Start in New York City, NY

Starting in NYC means embracing the hustle and bustle of the city that never sleeps. New York’s vibrant life—with pockets of calm, of course—means you’ll never be lost for something to do.

What to do

If that pocket of calm is what you’re looking for, try the Elevated Acre. Located on Water Street, this plaza-park combo rests on a skyscraper above the financial district. It offers beautiful views and events like outdoor movies and festival dances.
Homebodies who want a vacation away from home? This road trip’s for you too! Stick it to the quarantine blues with a trip to Brooklyn Boulder in Queens or Brooklyn. As the name suggests, this is an indoor rock-climbing area that lets you stretch your body without bugs zipping past your head.

Where to eat

Watermark Bar sits on the East River and overlooks the Brooklyn Bridge, giving extra fairy vibes at nightfall. You can eat outdoors or within the glass houses lit in pretty blues and whites. With reasonable prices, great food, and ping pong tables, the casual scene is a great rest area before you hit the road.
A fisheye view of the Brooklyn bridge leading into New York City at sundown.
Brooklyn, New York City, New York

New York to Harrisburg, PA

Driving time: About 3.5 hours
That calm puts you in a great headspace for the next leg of the trip. Travel almost 170 miles to end up in Harrisburg, the state capital of Pennsylvania. Harrisburg has a vibrant art scene and the homey feel of local businesses nestled in the city limits. With natural splendor like the Susquehanna River and ornate architecture like the Rotunda, there’s something for everyone to enjoy here.

What to do

City Island is known for its outdoor activities, from baseball games to carriage rides. For some friendly competitive fun, try the Water Golf course. You can cross its mini bridges and avoid the inner rivers, but do you have what it takes to win? That’s up to you!
If you want culture, find it at the Art Association of Harrisburg. This gallery has a history dating as far back as 1926. Exhibits occur year-round and you can schedule a class on pottery, watercolor, photography, and other mediums to interact with.

Where to eat

The Broad Street Market is a staple in Harrisburg. While it’s not a traditional restaurant, the numerous vendors provide both grocery supplies and full meals at their stations. Browse the culture and diversity of Harrisburg just wandering through their aisles!
A sepia-toned view of the a bridge over the Susquehanna River in Harrisburg.
Susquehanna River, Harrisburg, Pennsylvania

Harrisburg to Lexington, VA

Driving time: about 4 hours
Grab your snacks and buckle up for a drive to picturesque Lexington, Virginia. Near the Shenandoah Valley, Lexington is a hotspot for the old and young with its gorgeous nature, fun museums, and cool restaurants.

What to do

Stretch out those limbs on a hike through the Natural Bridge State Park. The primary trail takes you across a limestone bridge and provides a sneak peek into Saltpeter Cave. There’s a chance for fishing near Cedar Creek and a time to learn about the history of the Monacan Native Americans.
Speaking of history, Lexington is chock-full of museums and houses that belonged to historical figures. University Chapel & Museum and Miller’s House Museum are both good options.

Where to eat

Try out Bistro on Main that’s located, as expected, on Lexington’s main street. With a two-dollar sign menu, the bistro offers southern cuisine like gumbo or even shrimp and grits. They also wander outside of the southern hospitality expectation with dishes like the NY strip.
People traverse a concrete walkway that leads under the bridge of Natural Bridge State Park, Lexington.
Natural Bridge State Park, Lexington, Virginia

Lexington to Boone, NC

Driving time: about 4 hours
Located near the Blue Ridge Mountain, Boone is known for its forests, rivers, and everything in between. Explore the caverns, take a spin through the craft venues, and get to know the city named for famous pioneer and explorer Daniel Boone.

What to do

For outdoor adventure you have plenty of options. Hike along the Blue Ridge Mountains, take a trip down the Appalachian Ski Mountain, or travel back in time with the Western-style Tweetsie Railroad.
For some interactive fun, visit the Mysterium Escape Adventure. As the main hub for escape rooms in Boone, MEA has themed spaces able to fit up to eight players. Immerse yourself in the mystery and find the clues needed to be free!

Where to eat

Order takeout from Sunrise Grill, a cute restaurant that exudes a mom-and-pop feel. Try the scrambled eggs and hashbrowns, or opt for one of their many other lunch options. They currently specialize in takeout, which gives you extra flexibility if you want to enjoy your meal at a nearby park.
A vibrant orange sunset sweeps over the Blue Ridge Mountains in North Carolina.
Blue Ridge Mountains, North Carolina

Boone to Nashville, TN

Driving time: about 6 hours
The last leg of the trip takes you six hours into Nashville, Tennessee. Nashville is known for its Country Music Hall of Fame, music row district, hot chicken and biscuits, and more. And while you’ve had loads of fun on your way here, there’s still plenty to do!

What to do

Nashville Kayak Adventures allows you to stroll through downtown—on the water. If you’d rather explore without waves, take part in a mural art tour to explore Nashville’s street art by golf cart.
Become one with Nashville culture by trying your hand at a recording studio. Nashvox is a professional recording studio open to experienced musicians or newbies just wanting a taste of fun.

Where to eat

If you want to try the city’s iconic hot fried chicken, Prince’s Hot Chicken is the place for you. This eatery is known for its spice levels ranging from mild to ultra hot, as well as large portion sizes for family food.
Cars and pedestrians fill a Nashville street lined with fluorescent shop lights at night.
Nashville, Tennessee

When to go

In terms of weather, the east coast hits the highs and lows on every scale.
If you want to travel in more temperate weather, consider an early fall or late spring schedule. You’ll enjoy average temperatures with less rain—perfect for enjoying the natural splendor that this road trip includes.

Why you need roadside assistance

Remember the first step of the road trip? Pack everything. That includes plans for roadside assistance!
Traveling through mountains and cities has its hurdles, and leaving unprepared makes you vulnerable to flat tires, engine lights, or locking your keys in the car. Nothing will kill that road trip vibe faster!
The roadside assistance program from Jerry includes everything you need for peace of mind while on the road: up to 10 miles of towing, jumpstarts, key replacement, fuel delivery, and more—all for just $6.99 for one car.

How to find cheap car insurance

You’ll also want to make sure your car insurance policy is up to date before you hit the road.
If you’re looking for a new insurance company, Jerry can provide you with competitive quotes in under a minute. Swapping is just as effortless—Jerry takes care of all the paperwork, phone calls, and even cancels your old policy on your behalf!
“This app is all about savings! Jerry just saved me $193/month on my car insurance. They literally found me the cheapest policies out there and with better coverage! Seriously, just sit back and watch Jerry work its magic.” —Rachel B.
Haven’t shopped for insurance in the last six months? There might be hundreds $$$ in savings waiting for you.
Judith switched to Progressive
icon savingsSaved $725 annually
Alexander switched to Travelers
icon savingsSaved $834 annually
Annie switched to Nationwide
icon savingsSaved $668 annually

Easiest way to compare and buy car insurance

No long forms
No spam or unwanted phone calls
Quotes from top insurance companies
Find insurance savings — it's 100% free