8 Of The Most Hospitable Small Towns In Connecticut
If you are craving a quick escape or planning a whole vacation with easy access to major cities and plenty of natural spaces to explore, Connecticut packs a punch in hospitality. Take it to the next level, from upscale shopping and big-name brands to the spellbinding Philip Johnson Glass House from the 1900s with a glassy exterior.
MOCA Westport is an impressive contemporary art museum for visual and performing arts in a vintage castle-inspired venue. Essex inspired Stars Hollow in Gilmore Girls, while Darien exudes good vibes as the state's youngest population town without a college. Weston is a hiker's dream, with Devil's Den Preserve, Great Ledge, and the Katharine Ordway Preserve under 10 minutes away.
Darien
Darien, the Connecticut Gold Coast's smallest town, is surely hospitable, with a concentrated amount of fun attractions, services, and historic sights that will have you prowling alongside the friendly locals. Home to a fantastic town center with a warm aura of history, it is a perfect getaway to cool down for solitude seekers, bond with loved ones, or meet new friends. Its prized gem, the South Norwalk Historic District, is revamped with new businesses and eateries for a unique mix to browse Darien's historic profile of an old-architecture neighborhood, with scenically-old building views over amazing bites from the terraced cafes.
Across the Long Island Sound from New York, Darien exudes good vibes as the state's youngest population town without a college, with a fantastic array of affordable activities reflecting its clientele, which makes it one of the most fun and budget towns to visit. Blending heritage sights with its youthful spirit, Darien is a unique town to discover, including one-of-a-kind attractions for the whole family. The scenic Salt Cave of Darien, filled with Himalayan pink salt, boasts popularity for its healing powers and rejuvenation in an idyllic spot to relax in pretty sights. Don't miss the local Lock City Brewing Company for a variety of fresh-poured brews in a taproom over board games and live music.
Essex
Essex, one of the most popular towns to visit in the state, comprises several villages, so there's a lot of hospitality to go around. Nestled along the Falls River, on its way from the hills in the east, Essex is also just a few miles from Long Island Sound, with water recreation abounding in a fruitful region of majestic trees and gardens adorning fascinating architecture. From the resplendent waterfront for daytime strolls to a plethora of water activities for adventurers on both the river and the sound, no wonder this welcoming port town attracts scores of summer tourists. Visitors can mingle along the Federal, Victorian, and Cape Cod houses during the Groundhog Day parade, revealing the exuberant character of the town.
Its beautiful churches, like the First Baptist Church of Essex in the Egyptian Revival style, one of three in the United States, and the historic factory homes in Ivoryton, Essex, inspired the "Gilmore Girls" show's Stars Hollow! Home to the Town Hall from 1892, the samaritan spirit prevails in preserving the Yankee past, engraved in tradition, where the surrounding authentic farm structures date back as far as the Revolutionary War. Hosting the Burning of the Ships Parade, reminiscent of 1814, when 29 ships burned in the harbor, with more to learn at the Connecticut River Museum, don't miss a ride on the Essex Steam Train, an old-fashioned tour of several towns to soak up the nostalgic feel.
Madison
Madison, a darling little town incorporated in 1826, was named after the fourth president of the US, James Madison. Come for the natural surroundings and fascinating history intrigue, and stay for the welcoming feel that encourages you to explore. Home to a bout of quaint cafes and charming galleries in between local restaurants, visitors can enjoy lovely experiences in 19th-century buildings, some on the National Register of Historic Places. The idyllic Long Island Sound offers panoramic views of the waters and many fruitful outdoor spaces, like a bike ride or stroll along the Shoreline Greenway Trail.
Hammonasset Beach State Park offers a refreshing year-round escape for boardwalk strolls and bustles in the hot summer. Welcoming up to one million annual visitors looking for R&R like fishing, swimming, sailing, biking, and picnicking, you too can sunbathe or snuggle in a shaded spot with your loved ones in a picturesque frame of nature! Meigs Point Nature Center invites insights into the local fauna and flora all around, while the downtown offers entertainment and a unique shopping scene. Don't miss Audubon Shop or R.J. Julia Booksellers and take in a one-of-a-kind independent film at Madison Art Cinema.
New Canaan
Just an hour from New York City, this small-town commuter haven in Fairfield County offers an easy getaway to decompress. With a big downtown core, its sweet spot, the renowned Elm Street, is a destination in itself, where endless strolls will take you alongside upscale shops, cafés, and restaurants. While the prices reflect the clientele of the affluent community, plentiful ice cream stores will keep the kids happily tugging along. New Canaan's local art scene is to die for, including street art and especially the spellbinding Philip Johnson Glass House from the 1900s, with a glassy exterior, a unique take on modern living, and a pastoral 49-acre landscape.
Exuding good vibes, New Canaan embodies a new-age feel and a high society that is accessible to everyday tourists on a quick escape. Get in on its amazing shopping, admirable houses, and some of the state's best dining, like The White Buffalo, Sole, and Chef Luis. Home to 20,600 friendly residents and some of the highest median incomes in America, New Canaan extends its warmest welcomes through brand-name stores like Ann Taylor and J. Crew and the unmissable Silvermine Arts Center for hundreds of unique pieces of lovely art—some real conversation starters!
Niantic
Gracing both the Niantic Bay and the Niantic River, Niantic is a small coastal oasis on the Long Island Sound in Connecticut. With its spectacular waterfronts for a scenic stroll, locals enjoy dips at the first hankering. Home to the largest hobby kayak store on the East Coast, Three Belles Outfitters, Nianticans are a real know-how when it comes to boating, fishing, kayaking, canoeing, and water skiing. The carefree lifestyle pulls you in to trail in the wet footsteps for a swim at McCook Beach and a spectacular fresh seafood feast at Skipper's Seafood after. Offering what you expect and more of a seaside village, it is a great place to visit with your whole family, kids and pets included.
Nature prevails at Rocky Neck State Park, while places like the Children's Museum of Southeastern Connecticut are great for a whole rainy day of fun along its 5,000-square-foot facility of interactive discoveries. From local mingling in the day to romantic strolls at sunset along the Niantic Bay Boardwalk, the man in your life can choose from exciting fishing adventures, like Striper Snax or the Black Hawk, for a full or half-day excursion deep into the sea and not come back empty-handed. Meanwhile, the girls will enjoy a selection of unique and funky shops, like the immersive The Book Barn, with over 350,000 titles, including rare and out-of-print books.
Old Saybrook
One of Connecticut's oldest, most scenic, and hospitable towns, there are too many accolades to list in this once-home of the actress Katherine Hepburn! Dubbed "Kate" after the Oscar winner, its Cultural Arts Center is a legendary destination on a national scale, while the legend's former mansion sits overlooking Long Island Sound on a peninsula. With more Hepburn sites and thematic attractions, you can prowl along more high-end real estate envy on a scenic walk to the Lynde Point lighthouse. The beloved Harvey's Beach offers a calm atmosphere with clean waters and lapping surf onto the shallows of the soft-sanded stretch against the expansive views.
The cutest private golf course welcomes friends for a round of golf, while the historic Florence Griswold House is an inviting museum overlooking the sparkling Lieutenant River. Just behind, find the modern Robert and Nancy Krieble Gallery with inspiring works before scavenging the great restaurant scene with coffee roasters and the Monkey Farm, serving up fresh-caught local seafood. Small shops abound in vintages and antiques along the charming Main Street, while Rocky Neck State Park, 12 minutes east, is the town's favorite gym in nature, or a whole unforgettable summer's day worth of fresh air recreation and a beach.
Weston
Not to be confused with the town below, Weston is a wild animal in the bunch of hospitable towns at the gateway to the Devil's Den Preserve, Great Ledge, and the Katharine Ordway Preserve! As a real little cultural hub of the state, there are plenty of ways for everyone to discover its best, even on a short trip, and fit in a few of its abundant natural attractions within 10 minutes. The immersive Devil's Den Preserve, the nation's largest national preserve, offers amazing bird watching along wildlife trails for every level of hiking. If nothing else, trek to the scenic cliffside called the Great Ledge for a panorama of the entire area to take in over a picnic, photoshoot, or a quick selfie and keep going.
Weston is a revered getaway for families, friends, and couples looking to bond and commune with nature while getting in some fresh air R&R. An underrated gem with the friendliest local "crowds" in Connecticut, home to only 10,000, it is a stranger to traffic that would ruin your scenic shots. Discover its most vibrant hotspots, like the prime mingling spot at the Town Center, filled with food markets, restaurants, and storefronts. Whether you're absorbing the vibes outside on a terrace or returning after a hike for a pub crawl, the prevailing hospitality will have you back at the square in the morning for coffee and shopping for yourself or browsing for souvenirs before the trip home.
Westport
The scenic town of Westport, only 50 miles outside of New York City, is a popular getaway in the state. Primed on Connecticut's Gold Coast, it is a real estate wonder overlooking the waterfront! An affluent community of some 27,000 warmly embraces visitors to enjoy the vibrancy downtown along the Saugatuck River on a getaway from the gray city. From big-brand shopping like Lululemon, Tiffany's, and J.Crew to top-notch restaurants like Bartaco along the riverfront, its Historic District is a great way to spend a few hours with river views and architecture dating from its roots in 1835.
Come for a serene afternoon at the Old Mill Beach or sunbathe at the stunning Compo Beach, and stay for a free outdoor concert at the Levitt Pavilion. The rebuffed library welcomes visitors for quiet browsing, while MOCA Westport boasts an impressive contemporary art museum for visual and performing arts in an art venue that rivals any in NYC with its vintage castle-like appearance. Westport Country Playhouse delights all ages with shows and performances on a Broadway-like stage with former presenters Paul Newman and James Earl Jones. For immersive nature, look no further than Sherwood Island State Park, which spans some 230 acres of panoramic trails to a beach.
If you've got the New England fever or the city blues, these spirited towns will quickly have you sorted out, although you may never wish to leave their welcoming embrace. From budget getaways to affluent communities, these towns don't distinguish between visiting families and Oscar-winning celebrities. With four beach towns, including a former celebrity home and one named after a former US president, these warm-hearted towns vie for tourist attention with an immersive, slower pace of life and an upbeat spirit, oozing hospitality around each corner.
