6 Main Streets Where Connecticut Comes Alive

Despite being one of America’s smallest states (it’s only slightly larger than Rhode Island and Delaware), Connecticut punches above its weight when it comes to memorable small towns with exciting main street attractions. Proud of their New England heritage, the best of these picturesque communities have gone all-out to preserve centuries of history and heritage along their main drags. Boasting classic old homes and vintage commercial buildings, they also offer unique opportunities to experience a slice of authentic small-town Americana. Take a trip to any of these six Connecticut main streets and you’ll learn why they’re among the most popular tourist destinations in the Northeastern United States.

Essex

Essex Main Street starts at the Connecticut River and is about as picture-perfect a New England setting as it gets. Located 105 miles southwest of Boston, this perfectly preserved maritime village, though only incorporated in 1852, was settled 200 years earlier by colonists from England and soon became a vital shipbuilding center.

This important connection is on display at the Connecticut River Museum. Housed in a former steamboat warehouse dating from 1878, its location at the foot of the town’s immensely walkable Main Street makes it hard (if not impossible) to miss. In addition to exhibits on shipbuilding and the devastating British raid of 1814, you can even board a working model of the Revolutionary War's "Turtle" submarine.

Another must-do, the Essex Steam Train & Riverboat offers vintage rail journeys through the scenic Connecticut Valley from its station just off Main Street. These classic train rides connect to fun riverboat cruises that sail past the famous Gillette Castle and also provide special themed events, including the North Pole Express and a Day Out With Thomas.

Finish your lively main street experience with a visit (or better still, a stay) at The Griswold Inn, built in 1776 and still going strong. From here, you’re just a short stroll to other historic buildings, including Ebenezer Hayden II House from 1795, the 1799 Grover L'Hommedieu House, and the Hayden Chandlery, built in 1813.

Guilford

Boasting a 12-acre village green along Boston Street, the town’s main drag, Guilford is home to one of New England's largest collections of preserved 17th and 18th-century architecture. Founded in 1639 by English Puritans just 35 miles from New Haven, Guilford Town Green was originally used for military drills and grazing before its transformation into a leafy park.

From the green, it’s an easy stroll to major Guilford attractions like the Henry Whitfield State Museum, Connecticut's oldest dwelling and New England's oldest stone structure (it was built in 1639). Other Boston Street must-sees include the majestic 1912 Guilford Trust Company building; the saltbox-styled Hyland House, built almost 200 years earlier in 1713 and now a museum; and the Thomas Burgis II House, built in 1735.

If you’re looking for an excuse to visit, September’s Guilford Fair is the perfect time. Held at the Guilford Fairgrounds and accessible off Boston Street, it’s the state’s second oldest such event and has been a major community draw since 1859.

Litchfield

The sprawling Litchfield Historic District certainly deserves its reputation as one of New England's finest surviving 18th-century towns. Centered around Litchfield Town Green where four thoroughfares converge, the town’s elevated position made it of strategic importance during the Revolutionary War and the War of 1812 when it became both a supply depot for American forces.

Several Federal-style mansions lining the town’s broad main avenues reflect the town’s importance, including Tapping Reeve House, built in 1773 on South Street and home to America's first law school. Also on South Street, the Litchfield History Museum features rooms with locally made furniture and displays about the town’s fascinating history (admission is free).

Also along South Street, Oliver Wolcott House was built in 1754and was the home of a signer of the Declaration of Independence, and the Oliver Wolcott Library, built in 1799. Venture along North Street and you’ll want to keep an eye out for Benjamin Tallmadge House (1775) and the former Litchfield County Jail (1812).

Mystic

Mystic's Main Street crosses the Mystic River via the famous Bascule Bridge, creating a downtown district that attracts day trippers and weekenders from places like New York City and Boston, both an easy drive away. Mystic developed into a major shipbuilding center in the 17th century, its downtown taking root along East and West Main Streets, with the Bascule Bridge now the main drag’s star attraction. Built in 1922, this drawbridge-like river crossing boasts an impressive 85-foot span that is raised and lowered multiple times each day (so have your camera ready).

There’s also no shortage of historic architecture on or close to Main Street. Highlights include pretty St. Mark's Episcopal Church, constructed in 1867, and the elegant old Whaler's Inn. Built in 1920, this boutique hotel is ideal for those wanting to spend a night or two within view of the bridge and the downtown core. Just a block south of the hotel, Mystic River Park offers fun (and free) summer concerts.

Ridgefield

Extending for nearly two miles through town, exploring lively Ridgefield Main Street is a great way to spend your downtime. Founded in 1708 and located midway between Hartford and New York City, the town saw action during the Battle of Ridgefield in 1777. In fact, you can still see a British cannonball wedged into the side of the Keeler Tavern Museum & History Center, built in 1713 and now a repository of artifacts related to the town’s rich history.

History and culture unite at the Aldrich Contemporary Art Museum on Main Street, too. In addition to its impressive collection of artworks, the museum includes the "Old Hundred" building, built in 1783 and worth visiting for its large sculpture garden. Fancy staying in this historic old town? Spend a night at the elegant West Lane Inn, an 1849 mansion just off Main Street that now serves as a classy boutique hotel.

Washington

The main routes in and out of Washington wind past numerous points of interest. Incorporated in 1779, this compact little town features several landmarks worth exploring. Highlights include the Congregational Church from 1801 and the Gunn Historical Museum with its displays of local artifacts set in an old home from 1813. The museum also offers a fun self-guided tour that takes in these and other Washington treasures, such as the Mayflower Inn & Spa.

This luxurious hotel occupies 58 acres of scenic countryside and, in addition to its charming rooms and cottages, boasts a huge spa, hiking trails, and the popular Garden Room restaurant. Just up the road, the satellite community of Washington Depot is worth visiting for its eateries, including the historic G.W. Tavern set in a restored 1850s building. Hickory Stick Bookshop and the Washington Art Association & Gallery are also worth a visit.

The Final Word

Whatever your travel style and leisure interests, Connecticut's liveliest small towns feature main streets that offer no end of fun things to do. Each town’s unique attractions and experiences provide plenty of excuses not just for a visit, but for a deep dive into their unique characters. Having read this story, we know you’ll agree that these six main streets are where Connecticut (and Connecticuters) come alive.