For many New Yorkers, an ideal weekend getaway should be a place to avoid the throngs, a place to indulge in some serenity, with perhaps a hint of the unexpected. Well, just such a weekend of discovery awaits in any of these six Connecticut towns and villages that are at most a two-and-half-hour drive from Midtown East. These picturesque venues will transport you to Colonial New England or the Cape Cod coast without sitting all day in traffic. Each offers an abundance of green spaces as well as a level of sophistication that’s sure to please discriminating New Yorkers. And, the icing on the cake: each has a downtown that is meant for strolling.

The Connecticut River sparkles in fall in Essex, Connecticut.

6 Perfect Connecticut Weekend Getaways From NYC

1. Essex Village

Stay: The Griswold Inn is a landmark that’s been an accommodation since 1776

A sense of bygone days pervades this historic village once noted for shipbuilding, where the first colonial warship of the American Revolution was launched in 1776. Amble along tree-lined streets, gazing at white picket-fenced, pristine properties. You’ll find myriad emporia to duck into along charming Main Street such as the sunny Essex Coffee and Tea Company with walls adorned with the works of local artists. (They serve a delectable cinnamon blueberry coffee cake.) Art buffs should stop in the artist-owned Verdigris Gallery where exhibitions include the creations of printmakers. For a well-crafted sandwich, try Olive Oyl’s, a former gas station that’s now a vintage-style take-out deli. Waterfront Main Street Park is bedecked with sweet gum, scarlet oak, and other trees, making for a relaxing picnic spot. For an intimate dinner, indulge in curried beef empanadas and a fine glass of red wine at The Griswold Inn’s Wine Bar.

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See More: Essex, Connecticut | Could You Live Here?

The much-loved Niantic Boardwalk.
*Photo Credit : Courtesy of the Connecticut Office of Tourism*

2. Niantic

Stay: The Inn at Harbor Hill Marina wraps guests in enchanting waterfront views

A trio of small public beaches greets visitors to Niantic, all fronting Niantic Bay on Long Island Sound. They each offer a perfect venue for sunset viewing. Also popular is the mile-some-long boardwalk that’s much loved by joggers and parents pushing strollers alike. Paralleling the boardwalk, Main Street is chock-a-block with tempting treats, whether it’s the homemade ice cream at Gumdrops and Lollipops or the pecan sticky buns at the Sift Bake Shop. With its outdoor patio that’s peppered with shrubbery and colorful blooms, Cafe Sol is an atmospheric breakfast/lunch spot. (They’re focused on wholesome ingredients.) Walk off all those calories at wooded Rocky Neck State Park that’s threaded with hiking trails. Just three miles from the village center, this park is noted for its sandy beach.

All Connecticut weekend getaways should include a dose of charm, and Guilford’s Town Green is quintessential New England.
*Photo Credit : Courtesy of the Connecticut Office of Tourism*

3. Guilford

Stay: At The Homestead Bed & Breakfast, the vintage blends with the whimsical

Guildford’s attractive Town Green dating to the 1600s is a standout. Meander the network of paved paths, past dozens of trees, taking the time to admire the surrounding centuries-old houses. Across the street, chocoholics can tame their cravings at The Village Chocolatier. Nearby, Paperscape Artworks offers everything from one-of-a-kind notecards to papermaking classes. Just over a mile from the town center, soak up the nature-scape along Chittenden Park’s short boardwalk that navigates through a lovely salt marsh that attracts numerous birds. Then continue walking to Jacobs Beach, where birders will be thrilled. It’s hard to find a more scenic spot for a casual meal than the patio seating at Pa’s Place, a wee stone house overlooking the harbor. (The smoked shrimp and crab salad wrap is scrumptious.)

See More: 5 Best Town Greens in New England

Highlights from a visit to Madison include ocean views.
*Photo Credit : Michael D. Wilson*

4. Madison

Stay: The Homestead Bed & Breakfast

Visit the side-by-side towns of Guilford and Madison as separate, relaxed getaways or as a combined, active weekend jaunt. If you’re a bibliophile, then the two-story, sun-filled RJ Julia Booksellers will be a delight. (They regularly host author readings.) Art aficionados can explore the more than two dozen mostly contemporary public sculptures peppering downtown, including a giant damselfly created by Leo Jensen. For sophisticated picnic fixings, order a cheese plate at Madison Cheese Shop and Cafe, then head over to any of three public beaches, easily accessible from downtown. Or dine at The Wharf Restaurant, just steps from the sands of West Wharf Beach. For the most spectacular waterfront vistas, visit Hammonasset Beach State Park, about three miles away. On this windswept peninsula are boulders from the last glaciation, myriad hiking trails, and abundant shelling opportunities.

See More: Spring Weekend in Madison, Connecticut

Outdoor dining at Delamar Southport’s Artisan restaurant.
*Photo Credit : Courtesy of the Connecticut Office of Tourism*

5. Southport Historic District

Stay: The Delamar Southport adorns its guest rooms with art from the owner’s (Charles Mallory) personal collection

Beyond bustling Westport and Fairfield, Southport’s Historic District evokes the chill vibe of another era. In the late 18th/early 19th centuries, Southport was a prosperous port town favored by merchants and sea captains who built manses in styles ranging from Greek Revival to Federal. Gaze at these stately dwellings as you wander about, also taking in those along the coast. The elegant Pequot Library presents more evidence of times gone by, such as original Tiffany stained-glass windows. Steps from the historic district, Southport Park is a small, bucolic woodland where their new short-loop trail offers interpretive signage. When you’re feeling peckish, check out the locally sourced dishes at Artisan (at The Delamar) just outside the district, or dine at Paci, an upscale Italian eatery set within a renovated former depot station once used to store produce. (Rosie’s meatballs are delicious.)

A visit to Ridgefield may include a stop at Weir Farm National Historical Park in nearby Wilton, Connecticut.

6. Ridgefield

Stay: The 17-room West Lane Inn is set in the town’s historic district

Dating to the early 1700s, Ridgefield is a charmer. Bordered by stately trees and splendid mansions, historic Main Street is sprinkled with plaques describing the town’s role in the Revolutionary War. On land once owned by Colonel Burr Bradley, a Revolutionary War leader, Ballard Park is perfect year-round, whether you come for the cherry blossoms or the glistening, snow-draped gazebo. Just three miles away, other lush properties offer sensory delights, including Seth Low Pierrepont State Park and Weir Farm National Historic Park. Art lovers will enjoy the exhibits at The Aldrich Contemporary Art Museum, while those who adore opera or modern dance can attend performances at the Ridgefield Playhouse. Notable restaurants span the gamut of tastes such as 850 Degrees for thin, wood-fired pizzas; Luc’s Cafe for its mussels; and Ross Artisanal Bakery and Cafe for yummy flourless mudslide cookies.

Jeanine Barone

6 Scenic Connecticut Weekend Getaways from NYC