Connecticut Towns That Make You Feel Like You Stepped Back In Time

Several Connecticut towns make visitors feel as though they’ve stepped back in time with their beautifully preserved architecture and historic charm. There are so many towns with colonial-era homes and classic town greens that reflect centuries of New England history. From areas with maritime heritage to areas with quiet rural beauty, these towns offer a glimpse into Connecticut’s past that still feels alive today.

Stonington

To experience coastal New England charm, stroll down the narrow streets of the Borough of Stonington. The Borough was chartered in 1801 by a special act of the legislature of the State of Connecticut and it’s the oldest Borough in the state. The streets are lined with gorgeous historic homes and businesses housed in historic buildings. If you’re looking to actually step inside a historic home, check out the Captain B. Nathaniel Palmer House, which was built in 1852.
Discover things to do in town: Things To Do In Stonington, Connecticut

Wethersfield

My favorite historic town that’s further inland is Wethersfield. Much like the Borough of Stonington, Historic Wethersfield is super walkable. You can find a lot of historic charm on Main Street from historic homes to businesses housed in historic buildings. There are also multiple historic house museums on this strip. While you can see a lot of colonial architecture on Main Street, be sure to also explore the side streets for more historic charm. If you’d like to stay in one of these historic buildings, check out the Silas W. Robbins House B&B.

Essex

Essex is a town along the Connecticut River that has a lot of maritime history. The town was first settled by Europeans in 1648 and it was a part of the Saybrook Colony. Today, the town is home to the Connecticut River Museum where you can learn about maritime history and the village is lined with beautiful historic homes and businesses inside of historic buildings! If you’re looking to stay in a piece of history, you can stay in the Griswold Inn.
Discover things to do town: Things To Do In Essex, Connecticut

Mystic

Mystic, Connecticut is the state’s top tourist town because there’s plenty to do and there’s a lot of historic charm. If you’re looking to really feel like you’ve stepped back in time, I’d recommend going to the Mystic Seaport Museum. If you’d like the historic charm without paying an admission fee, visit B.F. Clyde’s Cider Mill, the oldest steam-powered cider mill in the United States. For true historic charm around downtown, I encourage you to explore the side streets to see charming historic homes.
Discover things to do in town: Things to Do & Places to Eat in Mystic, CT

Norwich

Norwich was founded in 1659 and there several historic districts in town. There’s the Norwichtown Historic District, which is around the Norwichtown Green. That district has several historic homes around the green and two history museums. There’s also the Little Plain Historic District, which is very close to the stunning Norwich Free Academy (NFA). You’ll find Gilded aged mansions at Millionaires’ Triangle, which is also near NFA. There’s also Bean Hill Historic District that’s just off of I-395.
Discover things to do in town: Things to do in Norwich, Connecticut

Guilford

Guilford was settled in 1639 and it is full of historic charm to this day. The town has five different history museums to visit, including the Henry Whitfield House, which was built in 1638. The Henry Whitfield House is considered to be Connecticut’s oldest house and the oldest stone house in New England. There’s also a lot of historic homes near the center of town. Be sure to explore around the historic town green, which is surrounded by homes, shops, and restaurants.
Discover more to do in town: Things To Do In Guilford, CT

Old Saybrook

Old Saybrook is the oldest town on the Connecticut shoreline as well as the oldest English town name in Connecticut. There are a lot of historic homes throughout the town, but my favorite area to see historic homes is in the North Cove Historic District. which has houses dating from 1700 to 1807. Be sure to also check out the Old Saybrook Historical Society’s Hart House & Gardens along Main Street.
Discover things to do in town: Things To Do In Old Saybrook, CT

Old Lyme

Old Lyme is located across from Old Saybrook on the other side of the Connecticut River. In its early history, it had industries centered around fishing, shipbuilding, and a salt monopoly. Later, it became a summer resort and artists’ colony. You can enjoy many historic homes along Lyme Street and you can visit the Florence Griswold Museum to learn about the art colony that was there. If you’re looking to stay somewhere historic, check out the Old Lyme Inn, which is also on Lyme Street.
Discover more things to do in town: Things To Do In Old Lyme, Connecticut

North Stonington

North Stonington was first settled in the late 17th century and incorporated as a separate town in 1807, splitting from Stonington. The town developed as a rural farming community, with small mills supporting the local economy in the 18th and 19th centuries. Today, North Stonington retains much of its historic charm, with preserved colonial homes and old churches. To experience some of this historic charm, go into the historic village and grab a drink and pizza at Shunock River Brewery or go for a hike at Hewitt Farm.
Discover things to do in town: Things To Do In North Stonington, Connecticut

East Hampton was settled in 1648. Back then, it was mostly farms with houses, barns, crops, and livestock. In the 19th century, the town was known for its production of bells, which earned it the nickname of Belltown USA. If you’re looking to check out some of the towns historic charm, check out the Village Center and the Middle Haddam Historic District. To learn about the town’s history, visit the Chatham Historical Society.
Discover things to do in town: Things To Do In East Hampton, Connecticut

East Haddam

East Haddam, Connecticut was settled in the late 1600s and officially incorporated as a town in 1734 after separating from Haddam. The town prospered during the 18th and 19th centuries through farming, shipbuilding, and milling along the Connecticut River. It is also home to the historic Goodspeed Opera House, built in 1876, which became a landmark of American musical theater, and Gillette Castle, which was the home of William Gillette, the actor who played Sherlock Holmes.
Learn more about how to visit Gillette Castle: Gillette Castle State Park

Litchfield

Litchfield is a walkable historic town nestled in northwestern Connecticut. In Litchfield, you’ll find beautifully preserved historic homes that were constructed in the 1700s and 1800s. There are also plenty of restaurants and shops to explore in the historic center of town. You can even stay in some historic inns or check out the Tapping Revere Law School House to dive further into the town’s history.

Canterbury

Canterbury was settled around 1703 and incorporated as a town in 1707 after separating from Plainfield. In the early 19th century, it became nationally known for Prudence Crandall’s school for African American girls, one of the first of its kind in the United States. The town has remained largely rural, preserving much of its historic charm and colonial-era character. Be sure to visit the Prudence Crandall Museum, which is housed in the old school, to learn more about the town’s history.

West Cornwall

West Cornwall was developed in the early 18th century as part of the larger town of Cornwall. The village grew around the Housatonic River, where water-powered mills and ironworks supported the local economy in the 1800s. Today, West Cornwall is best known for its iconic covered bridge, built in the 1860s, which remains a symbol of the town’s historic New England character.

Falls Village

Falls Village, the town center of Canaan, was established in the early 18th century and became an important industrial hub due to its location along the Housatonic River. In the mid-1800s, the village prospered with the arrival of the railroad, which supported local ironworks and mills. Today, Falls Village retains much of its 19th-century charm, with many historic buildings preserved in its National Register historic district.

South Norwalk

South Norwalk was originally developed in the 17th century as part of the larger Norwalk settlement. It became an industrial and shipping hub in the 19th century due to its harbor and rail connections. In 1870, it was incorporated as a separate town with thriving factories, oyster fisheries, and a busy waterfront. In 1913, South Norwalk was consolidated back into the city of Norwalk, and today its historic district, known as SONO, is a vibrant area of preserved warehouses, shops, and restaurants.

Windham

Windham was settled in 1686 and incorporated as a town in 1692, growing into an important colonial center for trade and industry. In the 18th and 19th centuries, the town flourished with textile mills and manufacturing along the Willimantic River. A famous local legend, the “Battle of the Frogs” in 1754, adds a touch of folklore to Windham’s rich and colorful history. There are a lot of beautiful historic buildings along Main Street, such as the town hall, and at Willimantic Brewing Company, you can dine in the old Post Office building. To dive into the town’s history, check out the Windham Textile & History Museum.

Simsbury

Simsbury was settled by English colonists around 1660 and incorporated as a town in 1670 after separating from Windsor. The town played a role in early colonial industry, with ironworks and mills powered by the Farmington River during the 18th and 19th centuries. Be sure to visit the Simsbury Historical Society during your visit to see some beautiful historic buildings and some cool exhibits.