Best Towns To Stay In For A Trip To Connecticut

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Choosing the right place to stay can shape your entire Connecticut trip. From walkable town centers and cities to quiet countryside escapes, the state offers a range of great home bases for every type of traveler. This guide highlights some of the best towns to stay in and what each town has to offer to help you pick a spot that vibes with you and your interests.

Mystic, Connecticut

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Photo credit: Kailey MarcAurele.

Mystic has a ton of things to do and so much historic charm. There are multiple places to stay right in downtown Mystic like The Whaler’s Inn and the Steamboat Inn. Downtown Mystic is extremely walkable and there are so many great places to eat. It’s no wonder why this is the top tourist town in Connecticut.
Discover things to do in town: Things To Do & Places To Eat In Mystic, CT

Essex, Connecticut

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Photo credit: Kailey MarcAurele.

Another charming, historic town that’s great to stay in is Essex. Like Mystic, this town is very walkable and there are a lot of great dining options and things to do in the area. If you’re looking to stay in the heart of downtown Essex where you can simply walk out of your lodging to enjoy the town, The Griswold Inn is a great option. If you’re looking for a quiet getaway out of downtown, you can stay at Copper Beech Inn in the village of Ivoryton.
Discover things to do in town: Things To Do In Essex, Connecticut

Old Saybrook, Connecticut

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Photo credit: Kailey MarcAurele.

Old Saybrook is one of my favorite coastal towns in Connecticut because there’s so much to do from hiking and beaches to historic sites. The downtown is super walkable, which I love. There are also two historic lighthouses in the area. If you’re looking for a luxury stay, I’d recommend Saybrook Point Resort as it’s right on the water and they have plenty of great amenities. There’s even a unique lighthouse suite you can stay in.
Discover things to do in the area: Things To Do In Old Saybrook, CT

Niantic, Connecticut

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Photo credit: Kailey MarcAurele

Niantic is a beach town with various beaches, a boardwalk, parks, restaurants, and a super walkable downtown. While it’s a great spot to stay during a summer vacation, it is also worth visiting in the off-season when it’s quieter. The best spot to stay is the In at Harbor Hill Marina, which is right on the water.
Discover things to do in the area: Things To Do in Niantic, Connecticut

New London, connecticut

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Photo credit: Kailey MarcAurele.

If you’re looking for a mix of city and historic charm, New London is a great place to stay. There’s a lot to check out from lighthouse tours and historic sites to restaurants and bars. If you’re looking for a charming and historic stay, I’d recommend staying at the Inn at Ocean Avenue.
Discover things to do in the area: Things To Do In New London, Connecticut

Stonington, Connecticut

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Photo credit: Kailey MarcAurele.

Stonington Borough is a charming area that’s super walkable with multiple coastal access points, shops, restaurants, and even a historic lighthouse museum. I absolutely love the historic charm in the borough. Staying here also makes visiting Westerly, Rhode Island very easy as it’s only about a ten-minute drive to the Rhode Island border. A great spot to stay is The Inn At Stonington.
Discover things to do in the area: Things To Do In Stonington Connecticut

Simsbury, Connecticut

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Photo credit: Kailey MarcAurele.

Simsbury is a town that’s full of history and nature in northern Connecticut. Whether you’re looking to dive into history, go for a hike, or grab a bite to eat at one of their restaurants or cafes, this town has you covered. Some options for lodging are The Simsbury Inn and Simsbury 1820 House.
Discover things to do in the area: Things To Do & Places To Eat In Simsbury, Connecticut

Wethersfield, Connecticut

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Photo credit: Kailey MarcAurele.

Wethersfield, specifically Old Wethersfield, is one of my favorite historic towns to visit in Connecticut. This town is a great spot to visit year-round, and the Main Street area is extremely walkable with plenty of restaurants, shops, and even house museums to check out. They also have seasonal events like their Scarecrows Along Main Street in the fall. For a unique and historic place to stay, check out the Silas W. Robbins House.

New Haven, Connecticut

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Photo credit: Kailey MarcAurele.

New Haven offers a vibrant mix of history, culture, and coastal charm. Visitors can explore Yale University’s stunning campus, world-class museums, and renowned theaters, or enjoy the city’s famous pizza and diverse dining scene. Nearby beaches, parks, and the harbor provide easy opportunities for outdoor relaxation and waterfront activities. There’s even a historic lighthouse you can visit at Lighthouse Point Park.

Kent, Connecticut

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Photo credit: Kailey MarcAurele.

Kent offers a picturesque getaway in the Litchfield Hills with a charming village center and scenic landscapes. You can easily access the Appalachian Trail, discover the state’s largest waterfall at Kent Falls State Park, or browse local shops, galleries, and cafés. The Kent Collection offers various lodging options in town.

Litchfield, Connecticut

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Photo credit: Kailey MarcAurele.

Litchfield offers a peaceful New England escape in the northwest corner of Connecticut. The town has a scenic countryside and a classic small-town atmosphere. The town center is very walkable with plenty of restaurants and shops to explore. There’s also plenty hiking options nearby, inlcuding some cool stone towers. The Abner Hotel is a great hotel to stay in right in downtown. Another option is The Litchfield Inn if you’d prefer to not be right in downtown.

West Hartford, Connecticut

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Photo credit: Kailey MarcAurele.

Staying in West Hartford puts you close to a lively town center with great restaurants, cafés, and boutique shopping in Blue Back Square and West Hartford Center. Be sure to check out Elizabeth Park, which is home to one of the oldest municipal rose gardens in the country. The town also offers easy access to museums, theaters, and cultural attractions in the greater Hartford area like the Wadsworth Atheneum Museum of Art and the Mark Twain House & Museum. A nice spot to stay is the Delamar West Hartford.

Woodstock, Connecticut

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Photo credit: Kailey MarcAurele.

Woodstock offers a quiet, rural escape in northeastern Connecticut, also known as the Quiet Corner. You can enjoy outdoor activities like hiking, biking, and kayaking, or explore local farms, historic sites, and charming village areas. The town is also close to lakes and state parks, making it great for nature lovers. A great spot to stay in town is The Inn at Woodstock Hill. Be sure to check out the Roseland Cottage while you’re in the area and grab a baked good from the Bakery Barn.

Ridgefield, Connecticut

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Photo credit: Kailey MarcAurele.

Ridgefield offers charming small-town vibes with a vibrant arts and culture scene. Visitors can enjoy performances at the Ridgefield Playhouse, explore local shops and galleries along Main Street, or spend time outdoors on nearby trails and parks. The Weir Farm National Historical Park is worth checking out if you’re interested in history and art. The town also features great dining options.

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