8 Small towns in Connecticut like Stars Hollow


Small towns in Connecticut have always held a special place in our hearts, particularly those that bear a striking resemblance to the mythical town of Stars Hollow from the popular television series “Gilmore Girls”. Check out this 8 small towns in Connecticut like Stars Hollow.

These quaint villages are typically characterized by their close-knit communities, stunning natural surroundings and old-world charm. From Middletown and Essex to Wilton and Manchester, there’s something magical about small towns in Connecticut like Stars Hollow that make them so inviting.

Small towns in Connecticut like Stars Hollow

1. East Haddam

East Haddam Town

East Haddam is a small town located in Connecticut. It has a population of just over 2,000 people and has many attractions including the Legends Golf Club and the Haddam Historical Society Museum. The town was once a thriving mill town and it still has a few mills left, including the East Haddam Mill.

The mill is open to the public and has displays on the history of the town and the mill. There are also restaurants and shops in East Haddam.

The town is also popular for its annual Stars Hollow Festival, which celebrates the fictional community on the television show “The Gilmore Girls.”

2. Old Lyme

Old Lyme Town by Expedia

If you’re looking for a small town in Connecticut that’s reminiscent of the fictional town of Stars Hollow, you should check out Old Lyme. This town is located on the coast and has a lot of historic buildings. You can walk around town or take a scenic boat ride. There are also many restaurants and shops to explore.

The town is just like Stars Hollow, only with a more modern twist. It has charming shops, restaurants, and pubs that will make you feel like you’re in the show. Plus, the ocean is just a short drive away! It is a small town with all amenities.

3. Washington Depot

Washington Depot by Record Journal

, Washington Depot is home to around 3,600 people and it’s known for its Main Street which is filled with stores and restaurants. There are also plenty of attractions located in Washington Depot, including the Brookfield Zoo and the Harriet Tubman Presidential Site. Washington Depot is definitely worth considering since it is close to major cities but still maintain quiet atmosphere.

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4. Kent

Kent Connecticut by Mass Live

Kent is a small town in Connecticut that is known for its charming architecture, lively small businesses, and scenic countryside. It is a great place to live, work, and raise a family. The town was founded in 1799 by General Moses Kent and is home to the Kent Historical Society Museum.

There are many quaint shops and restaurants in Kent that offer something for everyone. The town is also close to major transportation hubs, making it easy to get around.

The town is located just outside of Hartford and has a population of approximately 3,000 people. It’s a great place to live for those looking for a slower-paced lifestyle. There are plenty of things to do in Kent, including hiking, biking, fishing, and birdwatching.

5. Essex

Downtown CT by Visit Connecticut

Small towns in Connecticut like Stars Hollow are great places to live. Not only are they quaint, but they also have a lot to offer their residents. Essex is one of these towns and it has a lot to offer its residents. For example, Essex has a wide variety of businesses that can serve its resident’s needs.

It also has a high school, library, and grocery store that residents can use. Additionally, Essex is close to major cities like Hartford and New Haven, so residents can easily access the resources they need.

The town is also close to many attractions, including the Rocky Ridge Ski Area, the Wethersfield Town Green, and the Foxwoods Resort. Essex is a great place to raise a family or retire.

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6. Durham

Durham in Connecticut

Durham is a small town in Connecticut that was once a stop on the Underground Railroad. Today, it is a popular tourist destination for people who love small towns and history. There are many businesses in Durham that cater to tourists, including a bakery, ice cream shop, and art gallery.

The town also has two restaurants: an Italian restaurant and a Chinese restaurant. Durham is within driving distance of many attractions, including the Mystic Seaport and the Foxwoods Resort Casino.

The town is also known for its beautiful scenery, including rolling hills and lakes.

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7. Willington

Willington in Connecticut

Willington is a small town in Connecticut that is often compared to the fictional town of Stars Hollow from the show Gilmore Girls. Willington is known for its quaint shops, beautiful countryside, and friendly people. It’s also home to several notable attractions, such as Willington Congregational Church and Willington State Forest.

With a population of only 5,566 people, Willington is a great place to live and raise a family. The town has plenty of activities to keep residents busy, including fishing, hiking, biking, and cross-country skiing.

8. Coventry

Coventry a historic village in CT

Coventry is a great place to live, work, and raise a family. The town is home to many businesses and attractions that make it a great place to visit. Some of the businesses in Coventry are Stars Hollow Bakery, Jillian’s Diner, and The General Store. The General Store is famous for its annual pumpkin festival.

Coventry also has many attractions that make it a great place to visit, including the Rocky Hill Wildlife Preserve and the Greenfield Village Museum.

Coventry is perfect for people who want to live in a small town with plenty of entertainment options.


Small towns are a rarity these days, but they’re definitely worth exploring for those looking for a slower-paced lifestyle with plenty of character. Consider some of the small towns in Connecticut that are known for their charm and beautiful scenery. From East Hampton to Simsbury, take a trip down memory lane and enjoy all that these charming towns have to offer.

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