Most Walkable Town Centers in Connecticut

Whether you’re shopping, searching for a great meal, or simply enjoying a stroll, the charm of a walkable New England town just can’t be matched. Connecticut is home to numerous town centers with waterfront parks, outdoor restaurants, vintage boutiques, and historic downtowns, for a day of safe, leisurely exploration.

New Haven

Home to Yale University and just a short 1.5-hour train ride from NYC, New Haven is one of the country’s most walkable cities. Due to its grid layout, New Haven is easy to navigate on foot. At the center of the city is the 16-acre New Haven Green park that is surrounded by beautiful architecture, churches, shops, and restaurants, including the #1 rated pizza in the US, Frank Pepe Pizzeria. 

Chester

Located on the hillside of the Connecticut River, this beautiful small rural town has a picturesque Main Street with beautiful architecture, restaurants, shops, art galleries, and the world-renowned Goodspeed Opera House’s local Norma Terris Theatre. Once you’re done strolling downtown, ride the Chester/Hadlyme ferry across the Connecticut River and visit the historic Gillette Castle, and picnic or go for a hike at the Gillette Castle State Park.

Ridgefield

Located in the foothills of the Berkshire Mountains in Fairfield county, a short one-hour drive north from New York City, Ridgefield is home to a bustling Main Street that sits alongside beautiful colonial homes. The town’s walkable downtown is home to locally-owned shops and boutiques, five-star restaurants, theaters, museums, and a community park are all within walking distance from one another. Nearby, visitors will find walking trails, lakes, and miles of country roads that are perfect for biking. 

West Hartford Center

West Hartford is well-known for its hiking trails and unique charm, filled with storybook-like houses and cobblestone downtown areas. With all the charm of a traditional main street shopping district, West Hartford Center is known for its quaint brick buildings and small city feel. With cafes lining the streets and little shops to explore, you can spend the afternoon roaming around. Close by is Blue Back Square, a well-known area of West Hartford where you can find live music and entertainment during the warmer months and plenty of holiday cheer during the colder ones.

Putnam

Located on the banks of the Quinebaug River, this quaint New England town has been re-inventing itself with an “Arts & Al Fresco” motif. A collection of restaurants and eateries, antique shops, a large outdoor patio with chairs and tables, a mix of both modern and mom and pop stores, bars, cafes, art galleries, and theaters line the downtown streets. The pet-friendly Putnam River Trail also runs for two miles through woodlands, parks, and the shopping district that is perfect for walking, running, hiking, and biking.

Old Greenwich

With a New England-beach-town feel, this quaint coastal town is home to charming little shops, restaurants, and fun-filled activities, as well as the perfect spot to view the New York City skyline.  

The heart of Old Greenwich is its business district on Sound Beach Avenue. Rows of perfectly lined shops and restaurants line this stroll-friendly street with benches for sitting, and plenty of colorful flowerpots. Visitors can dine at critically acclaimed restaurants like Le Fat Poodle, and Applausi Osteria, and shop at independently owned boutiques with some of the greatest finds from around the world.

Westport

Downtown Westport combines the quaint New England charm with architectural beauty and water views. The Main Street area is home to mom-and-pop shops, historical landmarks, eateries, and a variety of retailers including Theory, Vineyard Vines, Tiffany & Co., J. Crew, Anthropologie & Co, Urban Outfitters and many more. Check out the nearby beaches and state parks for a sunset stroll along the Long Island Sound. 

Experience the Best of Connecticut at Delamar

With convenient and dog-friendly locations throughout Connecticut, Delamar offers the best in gracious living and convenience. Our Southport, Greenwich Harbor, and West Hartford locations are located just minutes from the centers of vibrant downtowns. When you choose to stay at Delamar, you can rejuvenate with our great amenities and luxurious attention to detail at every turn. Book your stay with us today and enjoy the charm of these quaint New England towns in all their glory.