6 Connecticut Towns and 30 Ways to Enjoy Them Last Updated: August 2021
By Kim Knox Beckius
Six small towns... five reasons to visit each in summer. The math seems simple: that’s 30 reasons to plan a Connecticut getaway. But these suggested things to see, eat and do only hint at what awaits. There’s always something happening in these vibrant communities—something for you to discover. And no calculator can compute the joys of making a small town “your” place.
As a reminder, be sure to check each location's website for new safety guidelines and COVID updates before venturing out.
Live Large In Greenwich
Connecticut’s southwestern town is just a hop from Manhattan. Dock your yacht outside the Delamar Greenwich Harbor. Oh, you don’t own a yacht? This dog-friendly hotel offers free valet parking, or it’s a short walk from the Greenwich train station. It’s also just steps from the “Rodeo Drive of the Northeast.” Greenwich Avenue in downtown Greenwich is lined with hundreds of upscale shops, art galleries and restaurants. Even window shopping is exhilarating.
When it's time to stop for a bite, you'll find plenty of great food in Greenwich—including French cuisine. Try inventive, gorumet meals inspired by Southern France at l'escale or try the vast selection of juices, crepes, soups, sorbets, ice cream, sandwiches and salads at Meli-Melo.
For a little arts and culture, discover more than a dozen changing exhibitions in art and science annually, live animal marine tank, lectures, educational workshops, and more at the Bruce Museum.
Go Green in Guilford
Guilford has been thinking green since 1640. That’s when one of Connecticut’s largest—and loveliest—town greens was laid out. You may find events on this town green, like those put on by Guilford Art Center—a fantastic place for all things arts. If you're looking to get your hands dirty, (with clay or paint, that is) at the art center you'll find classes for adults and children, gallery programs, a shop of contemporary crafts and more.
A short walk from the green, step inside the Henry Whitfield House and be whisked back to 1639, when New England’s oldest surviving stone home was built for the settlement’s minister. This resilient structure is the granddaddy of Guilford’s architectural treasures. The town claims New England’s third-largest collection of pre-Civil War homes. The best way to experience Guilford’s historic district is, ironically, aboard a green transportation vehicle that still seems ahead of its time. Guilford-based Shoreline Segway offers tours daily.
A 1784 farmhouse with fields to wander and barnyard animals to experience is the perfect place to overnight. The kid-friendly B&B at Bartlett Farm is around the corner from Bluff Head Preserve’s scenic hiking trails. After a day of adventures, “put your rump on a stump” at The Place, where tree stumps are the ultimate green seating, and clams and lobsters roasted over a wood fire are smoky-delicious.
Be Inspired in Kent
When a tiny town supports two bookstores, it speaks volumes about how intellectually and culturally stimulated you’ll feel when you visit. Situated along the Housatonic River and home to one of Connecticut’s last covered bridges, Kent is a place to stretch your legs and your mind. Spring’s the time to see Connecticut’s most-visited waterfall at its most vigorous and to watch vintage engines sputter to life at the Connecticut Antique Machinery Association’s Spring Power-up in late April.
By summer, the shimmering cascades at Kent Falls or Macedonia Brook State Park is a perfect picnic backdrop. Stop in the village first for tasty sandwiches and treats to go at J.P. Gifford Market & Catering Company. With a Chicken Cutlet Apple Melt in your belly and the soothing rush of the falls in your ears, the urge to nap may be irresistible. But save sweet slumber for later, when you retire to your serene room at the Kent Victorian. There’s more to inspire you, including the whimsical, life-sized giraffe, elephants, horses, dogs and woodland creatures at Sculpturedale. If you’re lucky, you may get to watch sculptor Denis Curtiss welding his metal menagerie.
Get Grounded in Glastonbury
Earth, water, fire, sky: they’re the natural elements that calm and restore us. If you’ve been spending far too little time outside, the Connecticut River town of Glastonbury is your place to reconnect with our planet’s abundance. Start by rolling up your sleeves and picking your own strawberries, blueberries and more at enduring family farms like Rose’s Berry Farm. Starting in mid-June, Sunday breakfasts prepared with fresh, seasonal fruit draw crowds. In the afternoon, spend time leisurely browsing The Shops at Somerset Square for the perfect mix of indoor and outdoor shopping.
Stay at the Connecticut River Valley Inn, and the included three-course breakfast will fuel you for an active day. Plus, you’re just a short walk from Riverfront Park, which comes alive on Wednesday evenings in July when it hosts the Glastonbury Riverfront Music Series: a popular lineup of free concerts.
Any night of the week, season after season, you’ll applaud the sea’s bounty at Max Fish. From raw bar selections plucked from Connecticut’s prolific clam and oyster beds to seafood dishes prepared with devotion to freshness and sustainability, this downtown Glastonbury restaurant pleases, and late-night deals on drinks and bar bites can’t be beat. Looking for more nighttime spots? Try Rooftop 120 for live music, great food and cocktails, and of course, rooftop views.
Dive Into Mystic
Are you the feet-first or the headfirst type? Try Mystic, a historic shipbuilding village at the mouth of the Mystic River. It offers watery pleasures as gentle as watching boats drift by while you dine and as life-changing as high-fiving a beluga whale.
Some say it’s because the human body is 70 percent water that we feel most alive when we’re waterside. A sail aboard the two-masted schooner Argia—sun on your skin, wind in your hair, lighthouses in your view—will certainly awaken your senses. Nothing quite elevates your pulse rate, though, like an Encounter Program at Mystic Aquarium. Whether you don waders and bend at the waist to embrace a beluga, listen to a penguin’s heart with a stethoscope or even collaborate with a whale to make a painting, the interaction will be unforgettable.
Sometimes, though, you just want to lower your blood pressure. That’s when you book a room with a whirlpool bath at the riverside Steamboat Inn. Meet friends on the deck at Red 36 for lobster rolls, local brews and harbor views. Or, step back in time at Mystic Seaport, where the annual Antique & Classic Boat Rendezvous in July brings boating enthusiasts together to celebrate craftsmanship.
Step Back in Time in Putnam
A not-so-sleepy town in the northeast corner of the state, Putnam has a flourishing downtown, a thriving creative community and a knack for nostalgia. Even as new galleries, cafes and ventures like the Putnam Peddler’s Market—a lively, upscale flea market held one Sunday each month, May through October—have popped up, traditions run deep in this 19th-century mill town.
Long known as an antiquing destination, Putnam’s worth the journey just to marvel at the assortment of items from the past assembled by 350 dealers at Antiques Marketplace. One of Connecticut’s largest antique malls has three floors to browse, and it’s far from the only antique shop in town. Lunch at Deary Brothers/Mike’s Stand is a step back in time, too. Locals and visitors have lined up for 79 summers to feast on chowder, lobster rolls, burgers, fried seafood and ice cream.
The hottest ticket in town is whatever’s on stage at the Bradley Playhouse. This 114-year-old vaudeville theater is the intimate setting for community shows that rival professional productions. When you tuck in at the Mansion at Bald Hill in nearby Woodstock, a grand 1890s summer estate turned sumptuous inn and restaurant, you’ll drift off anticipating tomorrow’s limitless possibilities in Connecticut’s must-see small towns.
From her home in Connecticut, Kim Knox Beckius is the voice of New England Travel for about.com, a Yankee Magazine contributing editor and the author of books like Backroads of New England.