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Walkable Towns for Summer

Walkable Towns for Summer

Get out and enjoy the warm weather by visiting one of our many walkable towns. Connecticut’s small-town rhythm inspires new experiences. Strolling through unique boutiques create a poetic ambiance, where delightful wares and sourced-local fare offer a real breath of fresh air.

FAIRFIELD COUNTY

Greenwich
Greenwich may only be minutes away from Manhattan, but this shoreline community embraces its small-town charm. Stroll along Long Island Sound in Old Greenwich and admire nautical-themed beachfront properties – some centuries old – before heading toward the fashionable and very riche Greenwich and Putnam avenues. World-class shopping and dining – featuring Saks, Brooks Brothers, Baccarat and the comfortably stylish Greenwich Tavern, to name a few – will impress visitors with big-city expectations. Click here for places to stay in Greenwich.

New Canaan
Aside from being one of the top-earning communities in the country, New Canaan is also known for preserving neglected properties of historical significance. A tour of the town will lead you to the doorsteps of America’s most famous Mid-Century Modern houses, including Philip Johnson’s Glass House, a National Historic Landmark. The New Canaan Playhouse blends the past with the present; its building is from 1923, but it hosts a full lineup of new releases, including some movies in 3D. Click here for places to stay in New Canaan.

Westport
Recognized as an East Coast art mecca, Westport has plenty to offer to theaterphiles, gallery explorers and aspiring curators. Eclectic galleries line the streets of downtown, while vacationers in pursuit of seasonal live entertainment can catch a show at the riverside Levitt Pavilion. Once you’ve had your culture fix, walk down to popular destination Tavern on Main for the New England ambiance – and delicious cuisine-Connecticut is famous for. Click here for places to stay in Westport.

GREATER NEW HAVEN

Guilford
Visitors may feel like they’re stepping back in time as they walk through Guilford, said to have the third-largest collection of historic homes in New England. Five homes/museums include the Henry Whitfield State Museum, built in 1639, where docents lead talks on its historic artifacts. For an unusual perspective of Guilford, glide through the town center and marina with Shoreline Segway’s guided tours. Click here for places to stay in Guilford.

New Haven
America’s first planned city is one of the most enjoyable to explore on foot, with heritage proudly displayed at every corner. Downtown New Haven is packed with more than 50 national retailers and boutiques and the centrally located New Haven Green, a vital piece of Connecticut history since its completion in 1638. Hillhouse Avenue, hailed as “the most beautiful street in America” by Mark Twain, is another must-see. Click here for places to stay in New Haven.

Madison
Culture awaits just a few steps out the door in this small Connecticut town. “Walk the block” as you stroll along Main Street, head down Wall Street, then west to Station Square. View the Madison Sculpture Mile, the new train station and the Tuxis Pond Boardwalk. Farther east and west on Main Street are more lovely shops, restaurants, beaches and historic sites. Click here for places to stay in Madison.

LITCHFIELD HILLS

Kent
Don’t let its small population fool you: Kent’s possibilities for adventure are larger than life. Peer over the county at the top of Kent Falls, a cascading 200-foot waterfall perfect for wading, hiking, picnicking and leaf peeping. Back in town, a visit to the Kent Village Barn Shops off Main Street will act as a one-size-fits-all destination for shopping, dining and gallery viewing. Click here for places to stay in Kent.

Litchfield
In the early 20th century, Litchfield attracted new residents due to its popularity as an affluent resort community. The town green, established in the 1720s and bordered by two main roads is home to upscale restaurants, such as the oenophile-favorite West Street Grill, specialty boutiques and colorful fall foliage. Click here for places to stay in Litchfield.

Ridgefield
Colonial homes and landmark buildings nestled between modern-day establishments make Ridgefield’s famous mile-long Main Street a one-of-a kind destination. The central retail area is highly walkable, with a great combination of shops and restaurants. Click here for places to stay in Ridgefield.

RIVER VALLEY

Chester
Watch the world pass by on Chester’s quintessential Main Street, a winding lane with an assortment of shops and restaurants housed in historic buildings. Ride the Chester-Hadlyme Ferry, one of the oldest operating ferries in the nation, to Gillette Castle, or purchase a handmade craft from the Connecticut River Artisans Cooperative. Click here for places to stay in Chester.

Essex
Essex reflects an 18th-century maritime community. Stop by the Connecticut River Museum, and take a sunset cruise for a panoramic view of the Connecticut River. The Griswold Inn, built in 1776, supports a bustling taproom and wine bar. Click here for places to stay in Essex.

Middletown
Named “Most Romantic Main Street” by the National Trust for Historic Preservation, Middletown’s main lane has all the charm needed for a weekend getaway. Savor international cuisine at award-wining restaurants, browse local shops, walk along the riverfront or attend a performance at Wesleyan University. Click here for places to stay in Middletown.

West Hartford
Don’t sell West Hartford short by dismissing it as a suburb - this town has a vibe all its own that sheds Hartford’s big-city shadow. West Hartford’s plentiful parking allows you to leave your car and explore the city’s hot spots, from trendy shops to plentiful outdoor cares, on foot. Click here for places to stay in West Hartford.

MYSTIC COUNTRY

Mystic
Settled in 1684 on the banks of the mystic River, the village of Mystic has retained its charm and history. Once a booming 19th-century shipbuilding center, its connection to the sea remains strong and the sailing schooners still pass beneath the Bascule Drawbridge. The quaint town center boasts one-of-a-kind boutiques, art galleries, bookstores, sidewalk cafes and restaurants - most notably Mystic Pizza, of film-screen fame. Click here for places to stay in Mystic.

Putnam
Get in on Connecticut’s “hidden gem” with a visit to Putnam, where a lively main street attracts some of the best live entertainment, art displays and antiques shopping New England has to offer. First Fridays, which take place on the first Friday of each month, with live music, art exhibits and performances, run May through December, while the Downtown Gallery Stroll in spring and fall celebrates the changing season with cultural events. Click here for places to stay in Putnam.

Stonington
Take a breath of fresh sea air in Stonington Borough, and explore nearby shops and restaurants, without ever venturing far from a spectacular ocean view. If you’d like to have that view with a touch of history, make a visit to the Old Lighthouse Museum. In the mid-1800s it was a beacon for vessels approaching in the harbor from Long Island sound. Click here for places to stay in Stonington.