7 Towns in Connecticut With Rich History
Given its status as the fifth state to ratify the US Constitution – a landmark event that took place on January 4, 1788, in the state capital of Hartford – it won’t come as a surprise to learn that Connecticut’s small towns are rich in history. From the close to 400 years of colonial history in towns like Wethersfield and Guilford to village-like communities like Farmington and Milford, there are plenty of great reasons to get out and explore the "Constitution State." Uncover historic towns in Connecticut that feature some of the most authentic tourist destinations in New England.
Wethersfield
Wethersfield was the second town to be settled in Connecticut and boasts a rich history that stretches back over 375 years. Originally named Watertown in 1634 (after the town in Massachusetts), the name change to Wethersfield occurred just three years later. Today, this living museum is home to the Wethersfield Historical Society, popular for its fun guided walking tours along Main Street. Along the way, you’ll learn of Wethersfield’s involvement in the country’s first witch trials, which predate those of Salem.
The nearby Webb-Deane-Stevens Museum is another must-visit and consists of three old homes dating from the 18th and early 19th centuries. The historic Chester Bulkley House Bed & Breakfast, just a few doors away, is a great spot for a romantic overnight stay in Wethersfield.
Guilford
Guilford is just a few miles east of New Haven. This charming coastal town was established in 1639 and named (though not spelled the same) after its namesake in England. The focus of a visit should be Guilford Historic Town Center, home to over 60 important historic landmarks that have been carefully preserved for posterity. One of the oldest, Hyland House, is an immaculately preserved saltbox-style home dating back to 1660 and now serves as a museum with exhibits about the town’s colonial past.
From here, it is only a short walk to Guilford’s lovely town square, a picture-perfect New England landmark that’s fun to explore for its boutique shops and restaurants. Other places to visit in Guilford include the Henry Whitfield State Museum, set in a home dating from 1639, and Chaffinch Island Park, a great green space for pleasant seaside strolls.
Chaplin
One of the "newer" communities, Chaplin was founded in 1822 and named after a local church deacon. The highlight of a visit is exploring the Chaplin Historic District, a charming village-like area along Chaplin Street. Popular sightseeing opportunities here include the Congregational Church, built in 1815; the red-brick Witter House, built in 1820; and the former Town Hall, which dates from 1840. There’s even an old Eaton’s store building that has stood here since 1850.
Other attractions include the Chaplin Museum, a small facility dedicated to local history; and Diana's Pool, a popular fishing spot and scenic viewpoint on the Natchaug River that’s especially popular when the fall colors arrive.
New Canaan
Widely considered one of the best places to live in Connecticut, New Canaan was founded in 1731 and boasts plenty of interesting historic buildings to visit. While at first an agricultural town, the American Revolution saw New Canaan become a center for manufacturing the shoes and boots needed for the military, a legacy that continued long after the war ended. The New Canaan Museum and Historical Society does an excellent job of portraying this and other important historical facts about the town.
Another popular thing to do in New Canaan is visiting The Glass House. Built in 1949, this stunning structure is a marvel of modern design and features transparent glass walls that allow unobstructed views of its interior and the surrounding landscape. Waveny Park, a sprawling 300-acre green space with an open-air pool and tennis courts, is also worth a visit.
Old Saybrook
While Old Saybrook is known to have been settled as a plantation as early as 1635, its town status wasn’t made official until 1738. Situated at the mouth of the Connecticut River, it’s certainly a pretty place to explore. Start your historical exploration in the Fenwick Historic District. This 195-acre site is included on the National Register of Historic Places and is home to 60 buildings, including a number built in the regional “shingle” style. The Fenwick Golf Course, one of the oldest in the country, can trace its roots back to the late 1800s.
Although situated offshore, Saybrook Breakwater Lighthouse, constructed in 1886, makes for a stunning photo. Harvey’s Beach is the go-to for sunseekers visiting Old Saybrook. It is ideal for swimming, sunbathing, and leisurely coastal walks.
Farmington
Just 10 miles west of Hartford, Farmington was incorporated in 1645 and was named after its rural farmland setting. Dubbed the "Village of Pretty Houses" by George Washington during his visit in the Revolutionary War era, there is no end of fascinating historical attractions to see here. Topping most lists is the Hill-Stead Museum, an architectural marvel built in 1901 in the Colonial Revival style. Now home to a treasure trove of French Impressionist art, this attractive 152-acre property features beautifully manicured gardens to explore.
The Farmington Canal Heritage Trail is a must-do and is a 54-mile-long scenic hiking and biking route that passes through the town and winds to the Massachusetts border. Other highlights include Stanley-Whitman House, the town’s oldest home (it was built in 1720), and the scenic Farmington River.
Essex
Essex is located on the Connecticut River and is another historic small town worth including on a Connecticut travel itinerary. One of the "newer" towns with a rich history, it was originally a part of Saybrook before becoming a separate town in 1854. These days, Essex is considered the "Perfect Small American Town" for its New England coastal vibe. The Connecticut River Museum is a must-visit attraction and was established in 1974 to educate visitors on the significance of the town and the river to the development of the state. In addition to its fascinating displays and collections, the museum's grounds provide a beautiful waterfront view over the town’s harbor.
The Essex Steam Train & Riverboat is also worth visiting. Founded in 1868, this historic site offers a range of experiences, such as railbike trips, train rides, and riverboat cruises. The historic Griswold Inn, dating back to 1776, offers a great afternoon tea service.
From the important museums of Wethersfield to the historic New England charm of coastal towns like Old Saybrook and Guilford, Connecticut is home to some of the best places to visit in the US for history buffs. Each of these seven charming old towns offers a unique journey through America's rich history and past and serves as an ideal getaway destination for those looking to learn more about this beautiful corner of the country.
