Charming Towns to Visit in the Tri-State Area (2024)

As the New York City area continues to reopen, everyone’s thinking about ways in which they can get a change of scenery. Whether it’s dining al fresco, taking a new walk, or exploring a new place outside of their neighborhood or town, people are itching to go somewhere different.

Below is a list of our favorite charming, small towns in the Tri-state area. Perfect to visit on a day trip or weekend get-away (depending on where you live), there’s just something about picturesque, small towns that makes exploring so much fun.

Connecticut

Kent

I remember an old friend of mine said that someday she’d live in Kent. A Connecticut girl myself, I had never visited Kent and didn’t know anything about it. After finally taking a trip there a few years ago, I get it. I absolutely love Kent! Located in Litchfield County, Kent is pure country small town perfection, surrounded by rolling hills, farm land, red barns and bucolic countryside. The town itself is low-key, tasteful, and full of antique stores, book stores, galleries and restaurants. There’s a ton of outdoor activity to do in the Kent area as well, including Kent Falls State Park for a hike up to its waterfalls. Check website for updates in regards to Covid-19.

Cornwall

If you’re in the Kent area, you must take a drive in and around the town of Cornwall as well. Make sure to drive through the impossibly charming “covered bridge”, that runs over the Housatonic River. Cornwall is known for it. My suggestion is to just drive around Cornwall and take in the beauty of it. The town itself is very sleepy. Many know Cornwall as home to Mohawk Mountain, the town’s beautiful back-drop. If you’re looking to go kayaking or canoeing, check out Clarke Outdoors.

The towns of Washington and Litchfield are beautiful as well. The famed Mayflower Inn & Spa is located in Washington and has long been a weekend retreat for Tri-State area folk looking for a nearby get-away.

You may also enjoy: A Day in Beautiful Litchfield County, CT

Madison

You would almost think you’re on the Atlantic Ocean in this beachy, seaside town in northern Connecticut, with its Cape Cod houses and tall, swaying seagrass – but nope, it’s on the Long Island Sound. Just as fine, though, as it feels and looks like a real ocean beach town. Madison has come to be one of my favorite places, as it’s not far, easy to get to, has 3 different beaches, and the overall vibe is beach chill. The Madison Beach Hotelis wonderful, and, FYI, it takes dogs. You can read more about the town of Madison in my post here.

Mystic

Mystic is situated on the Mystic river with a quaint main street and seaport. This maritime village is famous for being the setting of the movie Mystic Pizza; it’s also famous for being the home to the Mystic Aquarium. Though the inside is still closed, the outside exhibits are now open. But even if you don’t want to visit the aquarium, no worries – watch the draw bridge go up and down, wander the streets, eat lunch at one of its outdoor restaurants, and grab ice cream afterwards. We have taken day trips to Mystic without visiting the aquarium and it’s still just as splendid!

Stonington

Not too far from Mystic, and right before you cross over into Rhode Island is the tiny, but very charming town of Stonington. It’s the only place in Connecticut that faces the Atlantic Ocean. Its main street, Water Street, has all the seaside town staples – galleries, gift shops, ice cream stores, and most notably some excellent restaurants (try the Water Street Café). At the end of Water street there is a tiny public beach in which to enjoy the sea. Stonington feels very secret and off the beaten path, and that’s what I really enjoy about it. You can read more about it in my post here.

New York

Cold Spring

Cold Spring is one of the more unique towns I’ve visited. Set on the Hudson River, with the Storm King Mountain looming in the distance, the views are spectacular and dramatic in a way that you wouldn’t quite expect in a small town on the Hudson. The most popular things to do here are dining (there are a ton of good restaurants), antiquing (Cold Spring is filled to the brim with antique stores), and hanging out on the town green by the river. Just sitting on a blanket and taking in the views are enough reason to visit this awesome little town. You can read more about it in my post here.

New Paltz

I just discovered New Paltz last summer when I was doing a day trip to Mohonk Mountain House (yes, Mohonk accepts day visitors). What a cool town. Located in Ulster County, New Paltz is a college town (home to State University of New York at New Paltz) and has an authentic, young and hip vibe. There are design stores, vintage record stores, old-fashioned bookshops, country stores, and plenty of good food. Set in glorious Ulster County countryside, New Paltz is a gateway to outdoor activity, including hiking, biking, and water sports.

You may also enjoy: Mohonk Mountain Day Pass – Everything You Need to Know

Woodstock

Artists, musicians and writers have always flocked to Woodstock, even before its 60’s festival fame. Peace, love and happiness may be the underpinning themes here, but anyone who visits Woodstock takes a piece of that happiness with them, not just the hippies! Located in Ulster County in the Catskills, this scenic town is the perfect spot to stop after a morning hike, and enjoy its cheery atmosphere, window shopping and good restaurants. On the weekends make sure to check out Woodstock’s large outdoor flea market – it’s one of the best around.

Rhinebeck

Located in the Hudson Valley in duch*ess County, Rhinebeck exudes everything you think of when you think of Hudson valley cool – it’s a beautiful town where nature meets culture and the arts. Pretty tree lined streets, historic homes, B&B’s, museums, galleries, specialty stores and farmers markets all fill the streets of Rhinebeck, with majestic views of the Catskills in the distance. It’s totally worth a day trip or weekend get-away, as it has a lot going on in a divine setting.

Montauk

Everyone loves Montauk at the end of Long Island for its low-key, surfer vibe. Known for its gorgeous beaches, farmland, state parks, farmers markets, horseback-riding, biking and hiking, it’s a popular escape from New York City. It can take forever to drive there in the Hamptons notorious traffic, but once you’re there it’s a true escape from it all.

You may also be interested in: Why the Long Island’s North Fork Makes for the Perfect Weekend Get-away

Greenport

If the North Fork of Long Island is more your scene, check out the town of Greenport. It has a few hotels, a plethora of restaurants and shops, and it’s where you can hop on a ferry to Shelter Island. It makes for a great base in which to explore the wineries of the North Fork – the main reason why people come to visit. Spend a day wine tasting in the North Fork’s bucolic countryside, then head back to Greenport for a nice meal at one of its restaurants. Or you can spend the day at one of its low-key beaches.

New Jersey

I’m going to be honest and say I’m not all that familiar with New Jersey. I know it has some beautiful countryside, and obviously the shore, but I don’t really know the towns that well. I do, however, know Cape May, and it’s a gem.

Cape May

Many people consider Cape May the oldest seaside resort in America. Located on the southern tip of the Jersey Shore, this historical landmark town is nothing like its northern neighbors. Think Victorian homes and B & B’s, gas-lit lamp posts, horse-drawn carriages, trolleys and people sitting out on their front porches on their rocking chairs. Cape May actually has the second largest concentration of Victorian homes after San Francisco. It is an utterly picturesque and charming town, and I can’t recommend a visit enough. The beach is stunning and vast, and close to historical downtown.

You can read more about Cape May in my posts Cape May Historical District and the Best of Cape May with Kids.

Those are our picks for best small towns to visit in the Tri-State area. If you have any to add, please do so in the comments!

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