The Best Weekend Getaways in Connecticut

From pizza in New Haven to poker at Foxwoods, these are the best weekend getaways in Connecticut.
Written by Heather Bernhard
Reviewed by Kathleen Flear
Updated on Jun 01, 2022
Whether you opt for an overnight in New Haven or a long weekend in Hartford,
is the ideal place for that bite-sized vacation you’re craving. 
You know what they say—time flies when you’re having fun. That’s especially true when you only have a few days to fit in everything you want to do. 
Car insurance
knows just how important it is to have a plan for your precious vacation time. That’s why we’ve created this list of weekend getaways in The Constitution State. 
From foodie adventures and Ivy League universities to world-class hiking and family fun, these are the best weekend getaways in the great state of Connecticut. 
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The best weekend getaways for couples in Connecticut 

Old Saybrook

A small sailboat putters out of the mouth of the Connecticut River.
Stay at:
Saybrook Point Inn and Spa
(rooms from $265/night)
Quality Inn Old Saybrook - Westbrook
(rooms from $118/night)
If you stay at the Saybrook Point Inn, start your weekend off with a walk along the shoreline, then brunch at the charming
Fresh Salt
Next, spend your afternoon checking out the area’s local history at the
General William Hart House
and the
Fort Saybrook Monument Park
. Then, wrap things up with fresh, local seafood at
Liv’s Oyster Bar
Kick off day two with breakfast at local favorite
The Paperback Café
, then head to
The Katharine Hepburn Performing Arts Center
, the town’s most popular attraction
Spend your afternoon shopping on Main Street, and wrap up your weekend with a romantic dinner at Café
. Make sure to check out the Mood Lounge, where food is served tapas-style and paired with “sensory libations.”


Boats on the river at sunset.
Stay at:
Spicer Mansion
(rooms from $299/night)
Howard Johnson by Wyndham
(rooms from $152/night)
Start your Connecticut getaway by touring the Connecticut Wine Trail.
Saltwater Farm Vineyard
Stonington Vineyards
are great local options, and Saltwater often has live music and food trucks. 
Later, take a romantic sunset cruise on the schooner
and enjoy a late dinner at
The Shipwright’s Daughter
Begin day two with breakfast at a local spot (if you stay at the Spicer, make sure to check out their
!), then spend the day at one of Mystic’s many
Not a beach person? Stroll through historic downtown Mystic instead, and make sure to grab a slice at the famous
Mystic Pizza
. Finally, end your trip by sampling an age-old aphrodisiac at the
Oyster Club
Pro tip If you head to Old Saybrook, make sure to check out the 18th-century-style gardens located behind the General William Hart House. During the spring and summer, they are particularly magnificent with shrubs, roses, fruit trees, and flowers.

The best weekend getaways for families in Connecticut 


Aerial view of Hartford
Stay at:
Best Western Hartford Hotel & Suites
(rooms from $213/night)
Candlewood Suites Hartford Downtown
(rooms from $122/night)
Historic Hartford, Connecticut is loaded with things for the whole family to enjoy. Kids love the vintage carousel at
Bushnell Park
and the fun exhibits at the
Connecticut Science Center
. Meanwhile, parents enjoy the
Harriet Beecher Stowe House
, which features a children’s educational center where kids can try out various 19th-century activities.  
For family-friendly meals, grab a pizza at
or head to
Chowder Pot
for one of their famous lobster rolls (don’t worry, they have fried mozzarella for the kids). 


Stay at:
DoubleTree by Hilton
(rooms from $158/night)
Holiday Inn Cheshire
(rooms from $114/night)
For a slightly more adventurous weekend, head to Bristol, home of the country’s oldest theme park.
Lake Compounce
features dozens of rides, including the world’s 14th-oldest wooden roller coaster, Wildcat. Afterward, check out the
Witch’s Dungeon Classic Movie Museum
, an homage to the golden era of horror and sci-fi. 
If your kids are on the younger side, check out the children’s museum
Imagine Nation
or the
New England Carousel Museum
Looking for some grub? Try
Buster’s Drive-In
for some good, old-fashioned burgers and shakes, or
for some of the tastiest fried chicken in the area.  

The best weekend getaways for casino enthusiasts in Connecticut 

Foxwoods Casino (Mashantucket)

Stay at:
Hilton Garden Inn
(rooms from $132/night)
The Whaler’s Inn
(rooms from $325/night) 
There is plenty to do at Foxwoods without ever leaving the property: fine
, a spa,
, golf, and (of course)
. There are even attractions for the
little ones
, including bowling, an arcade, and ice skating. 
That being said, there is plenty more to see in the area. Just minutes from the casino, the
Mashantucket Pequot Museum & Research Center
is the largest Native American Museum in the world. 
If shopping is more your speed, check out the
Tanger Outlets
, where you can find discount prices at over 70 stores, including Nike, Coach, and Michael Kors.

Mohegan Sun Casino

Stay at:
Hyatt Place
(rooms from $128/night)
Mohegan Sun
(rooms from $208/night)
Mohegan Sun is right down the road from Foxwoods and offers just as much to do (you could feasibly visit both casinos in one weekend, in fact). While at the casino, you can choose from
43 different restaurants
, see a show at the arena, or catch some stand-up at
. Past acts at the theater have included acts ranging from Taylor Swift to Jon Bon Jovi. 
Off-site, check out the
Tantaquidgeon Museum
or drive a few miles to tour the historic
USS Nautilus
at the Submarine Force Library and Museum Association. Want to get away from the hubbub for a bit? Head to
Yantic Falls
for a short (but beautiful) hike.
Note: If you have risk factors for compulsive gambling, consider avoiding gambling in any form, people who gamble, and places where gambling occurs.

The best weekend getaways for foodies in Connecticut 

South Norwalk

Stay at:
DoubleTree by Hilton
(rooms from $105/night)
Residence Inn
(rooms from $170/night) 
South Norwalk is practically overflowing with restaurants: Edwin Montoya, the owner of French restaurant
Appétit Bistro
, calls the town a "foodie destination." It seems like no matter where you go, there is another place to eat. 
There are dozens of choices, from globally influenced
to Asian comfort food restaurant
Mecha Noodle Bar
to local favorite
O'Neill's Pub & Restaurant
While you're there, don't forget to check out
Burger Bar & Bistro
for “the best burger in the state.” Located just minutes from the
Maritime Aquarium
, it's a great place to go with the family after a long day out. 

New Haven

View Lighthouse Point, New Haven with the sea on the left and the beach on the right.
Stay at:
Graduate New Haven
(rooms from $206/night)
Courtyard New Haven at Yale
(rooms from $151/night)
New Haven is best known for pizza, but the food scene has more to offer. Locals love
Louis’ Lunch
, creator of the first hamburger, and
Miya’s Sushi
, the first sustainable sushi restaurant in the world. The
East Rock Brewing Company
is great for sampling some local craft beers and grabbing a bite to eat.
Of course, we’d be remiss if we didn’t mention the pizza: New Haven is known for having some of the best pies in the Northeast. People travel hundreds of miles to hit up the iconic
Frank Pepe Pizzeria Napoletana
Sally’s Apizza
Pro Tip Many of the restaurants in South Norwalk (or “sono”) are close together, so you can totally walk from one to another. Why not make a list of all the places you want to check out and set up your own foodie tour? 

The best outdoor weekend getaways in Connecticut 


Stay at:
Lake Compounce Campground
(sites from $32/night)
Passport Inn & Suites
(rooms from $80/night)
If you’re an outdoors enthusiast, Middlefield is the place to be. This small town doesn’t offer much in the way of hotels or restaurants, but it does have one of the most scenic hiking trails in Connecticut. 
The Mattabesett and Mount Higby Trail
is an 8.9-mile trail that runs along cliffs, allowing for several panoramic views of the Quinnipiac Valley (look for the CT Police Academy below!). 
Visit in the spring or summer to see some of the state’s beautiful wildflowers, or in the autumn for magnificent fall foliage. 
Pack a picnic lunch in case you get hungry, but remember: this is bear country! Keep everything sealed up.


Stay at:
Lake Waramaug State Park
(sites from $17/night)
Mayflower Inn and Spa
(rooms from $775/night)
Tiny Roxbury, CT has a little over 2,000 citizens and no “downtown” to speak of. What it does have is tons of country charm and some incredibly cool hiking at the
Mine Hill Preserve
A 19th-century iron mine and furnace complex site, Mine Hill offers abandoned mine shafts, a granite quarry, blast furnaces, and more to explore. Right down the road is
Lake Waramaug State Park
, where you can camp, fish, boat, and swim. 
Make sure to check out
while you’re in town. Locals rave over the friendly service and fantastic food (especially the breakfasts). 
Pro Tip Connecticut has hundreds of miles of hiking and biking trails, from easy to difficult and high land to low. Of note is the Appalachian Trail, which travels 52 miles in Connecticut, mostly following the ridges to the west of the Housatonic River Valley.

The best weekend getaways for history buffs in Connecticut 

Old Lyme

A seagull takes flight over a crowded beach in Old Lyme
Stay at:
Old Lyme Inn
(rooms from $159/night)
Pier Blue Inn
(rooms from $99/night)
Old Lyme was founded in 1655 when it separated from Saybrook. Early industry centered on fishing, shipping, shipbuilding, but in the early 19th century, the town evolved into an artists’ colony. Today, it remains a rich center for culture and the arts.
You can visit the
Florence Griswold Museum
, home of the former Lyme Art Colony, or the
Lyme Art Association
, which has been showing fine art exhibits since 1914. Round out your trip with some shopping in the
historic district
and a meal at the
Griswold Inn
, in business since 1776.


Stay at:
Hampton Inn
(rooms from $228/night)
(rooms from $92/night)
In 1655, a tiny trading post near Nod Brook on the Nashua evolved into The Plantation of Groton. Centuries later, many monuments to the town’s history still stand, such as the Groton Leatherboard Factory (opened in 1916) and a cemetery dating back to 1704.
One of the main draws for history buffs is the
Fort Griswold Battlefield State Park
, the site of the 1781 massacre led by Benedict Arnold. While there, you can tour the historic fort and stop by the
Ebenezer Avery House
, where patriots sheltered those wounded in battle. 
If you have time, stop by the
Avery Copp House
, which houses artifacts from the Revolutionary Era through both World Wars. 
And don’t forget to grab a bite to eat! If you’re a meat and potatoes person, check out the
Gibbet Hill Grill
for the perfect steak, or swing by
Salt & Light
if you’re in the mood for lighter fare.

The best cheap weekend getaways in Connecticut 


Stay at:
The Lloyd
(rooms from $161/night)
Amsterdam Hotel
(rooms from $95/night)
For the traveler on a budget, Stamford is full of cheap and free things to do. Start your weekend with a coffee and a scone at
Lorca Coffee Bar
—grab some extra snacks for a picnic later! 
Then, head to the
Bartlett Arboretum and Gardens
and spend your day exploring the 93 acres of hiking trails, gardens, and wetlands. Finally, end the day with a meal both your wallet and your tummy will love at middle eastern restaurant
Layla’s Falafel
The following day, grab a pancake tower at the
Elm Street Diner
, then check out some artwork for FREE! Start with the UConn Stamford Art Gallery, then head to
Stamford Art Association and Townhouse Gallery
. Round out your day with the
Whitney Museum at Champion
, then back to the Elm Street Diner for one of its famous extreme milkshakes.

New Haven - Yale Campus

Stay at:
La Quinta
(rooms from $98/night)
Holiday Inn Express
(rooms from $80/night)
Yale University
’s beautiful campus is one of New Haven’s biggest attractions. Grab a breakfast sandwich or tea, then take a free guided tour of campus (10:30 am, Monday-Friday, or 1:30 pm on weekends). 
If you’d rather explore on your own, pick up a Blue Trail Map at the Visitor Center for about $5 and stroll at your own pace. Wrap your day up with a trip to the
Yale University Art Gallery
, and then drinks, dinner, and live music at
Stella Blues
Continue your art tour the next day with a trip to the
Yale Center for British Art
, followed by the
Knights of Columbus Museum
. Grab an ice cream cone from
Arethusa Farm Creamery
, then walk around the historic
Grove Street Cemetery
the oldest cemetery in the nation
Before you leave, make sure to stop by
St. John the Divine
, which was built in 1863 to “civilize the miners.” The original walls, rafters, and handmade nails are still visible.
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