Whether you are looking for romance or relaxation, Connecticut is a perfect choice for a weekend getaway.
From seaside towns to nature retreats, each spot on this list is charming and steeped in history. With cute shops and great food, you can slow down but still make the most of a quick trip.
Read on to find an amazing weekend getaway in Connecticut!
Mystic
Mystic is a favorite of mine. Though once a bustling seaport, people now come here to relax near the ocean. You can sail away on a majestic schooner or even charter a private yacht!
If you prefer to stay on land, visit the Mystic Seaport Museum instead. They have a shipyard with historic boats and a recreated 19th-century seafaring village.
Take a pleasant stroll along the waterfront and pop into the locally owned shops on Main Street that sell antiques, jewelry, and much more.
For lunch, grab a slice at Mystic Pizza, the namesake of the 1988 movie featuring Julia Roberts in her breakthrough role (the restaurant was the inspiration, but they filmed in a different location).
Cozy DuBois Beach is a great place to watch the sun set, and then you can stop by the Oyster Club for some fresh seafood.
Where to stay in Mystic, CT: The Whaler’s Inn
Length of time from:
- Boston – 2 hours
- New York City – 2.5 hours
Chester
Chester is a beautiful town that radiates charm. If you need a break from city life, it will help you decompress in a more bucolic setting.
Take a delightful stroll down Main Street and visit galleries or cafes. If you want to be closer to nature, then hike the 2.7-mile loop around the Pattaconk Reservoir.
Gillette Castle State Park is in neighboring East Haddam and sits on top of the southernmost hill in a chain known as the Seven Sisters.
The 24-room castle was completed in 1919 for William Gillette, an actor who performed as Sherlock Holmes on stage and in a silent film. The state bought it in 1943, and it even contains a secret door leading to a secret room!
To fuel your vacation, you can get some pasta at Grano Arso or some ice cream at Honeycone (with seasonal flavors like chili chocolate and olive oil orange peel).
Where to stay near Chester, CT: Riverwind Inn
Length of time from:
- Boston – 2 hours
- New York City – 2 hours
Washington
Washington is a quaint town that sticks to a slower pace of life along the Shepaug River, making it a top weekend getaway in Connecticut. It served as inspiration for the creator of Gilmore Girls, and I love it here even more for that.
Hickory Stick Bookshop is a great place to stop and sits right across from the Washington Farmers Market. To better understand the history of the area, you can visit the Institute for American Indian Studies.
The gorgeous Hidden Valley Preserve has 700 acres of forest and meadows as well as the Henry David Thoreau Footbridge. You can also hike in the Steep Rock Preserve, which has an old railroad tunnel completed in 1872.
For another outdoor experience, drop by the Hollister House, a whimsical English garden that is formal in structure but wild in style of planting.
Whatever you decide, you will feel yourself unwinding in the peace of the environment.
Where to stay in Washington, CT: Mayflower Inn and Spa
Length of time from:
- Boston – 3 hours
- New York City – 2 hours
Old Saybrook
Old Saybrook is a cute seaside town where you can relax. The lull of the ocean is at every turn, and the atmosphere is serene.
You can walk on the soft sand of Harvey’s Beach and watch the sun set over the calm water. You can also hike in The Preserve, a 1,000-acre coastal forest with tons of wildlife.
Charming Main Street has stores that sell antiques, pastries, and much more. The Kate is a beloved cultural center named after Katharine Hepburn that hosts plays, films, and concerts.
In nearby Old Lyme, visit the Florence Griswold Museum, a bright yellow Georgian-style home with Impressionist artworks. The former boardinghouse hosted numerous artists in the early 20th century and many left behind paintings on the walls and doors.
You can end a day with some clams at Fresh Salt. Just remember to take a few more gulps of the sea air before you leave this haven!
Where to stay in Old Saybrook, CT: Saybrook Point Resort and Marina
Length of time from:
- Boston – 2 hours
- New York City – 2 hours
Kent
Kent is a tiny town with an absolutely stunning landscape, making it a top weekend getaway in Connecticut. We come here for a respite from our daily life and to get closer to nature.
The panoramic views are especially gorgeous in the autumn when the foliage burns with vibrant hues of red, orange, and yellow.
Kent Falls State Park has miles of hiking trails, and its namesake cascading waterfalls drop a total of 250 feet. You can also see Bull’s Bridge, a rare surviving covered bridge full of New England charm. It was built in 1842, and legend has it that George Washington used it during the Revolutionary War.
Back on Main Street, you can pop into House of Books, a lovely shop in a historic building. Kent Coffee and Chocolate is another cute spot, where you can get a caffeine fix with some handmade truffles.
Lastly, you can walk up the road to visit the Eric Sloane Museum. He was a prolific artist whose works celebrated the folklore of America.
Where to stay near Kent, CT: Homestead Inn
Length of time from:
- Boston – 3 hours
- New York City – 2 hours
Essex
Essex is a historic town full of charm. Though now a haven for peace and quiet, it was once attacked by a foreign power (the British in the War of 1812). It has homes that date back even further, with some constructed during the Revolutionary War period.
You can hop on the Essex Steam Train, which pulls vintage coaches through a quintessentially New England landscape. It even provides sole access to wetlands that are natural habitats for a variety of birds like blue herons and bald eagles.
Next, you can hop on the Becky Thatcher, a triple-decker riverboat that will show you the beauty of the Connecticut River.
Back on land, take a lovely stroll down Main Street to visit the quaint shops or walk even further to admire the harbor.
Lastly, be sure to stop at The Gris Tap Room, a beloved institution with casual American fare and live music.
Where to stay in Essex, CT: The Griswold Inn
Length of time from:
- Boston – 2 hours
- New York City – 2 hours
Litchfield
Litchfield is a picturesque town with an incredible historic district and village green.
A lovely white-spired church sits among preserved homes from the 18th century where you can step back in time. For example, Tapping Reeve House and Law School was the first in the nation, and its students went on to play foundational roles in our democracy.
Take a trip over to Topsmead State Forest, which has a Songbird Trail, an English Tudor cottage, and a Butterfly Garden. White Memorial Conservation Center is another sprawling testament to nature, great for hiking and photography.
In the summer, you can visit White Flower Farm, which has incredible displays of roses, dahlias, and many more. In the winter, you can ski on Mohawk Mountain.
We always make sure to hit Peaches n’ Cream before we head home, a gourmet ice cream parlor with flavors like salted pretzel caramel.
Where to stay in Litchfield, CT: The Litchfield Inn
Length of time from:
- Boston – 2.5 hours
- New York City – 2.5 hours
I hope this post gave you some ideas for a weekend getaway in Connecticut! As you can see, each vacation is drivable from Boston or New York City.
In terms of the most beautiful places in Connecticut, I think Old Saybrook and Kent are definitely up there.
I think the best weekend getaways for couples in Connecticut (and the best places to celebrate your anniversary in Connecticut) are The Whaler’s Inn in Mystic and the Mayflower Inn and Spa in Washington.
Now read about some amazing bed and breakfasts in Connecticut. If you want to go shopping while in Connecticut, then check out the outlets.
Enjoy!