5 Small Towns in Connecticut So Dreamy, You’ll Swear You’ve Seen Them on TV

Connecticut is no stranger to serving as a filming location or as inspiration for TV settings. Its classic pastoral scenes, combined with coastal options and New England magnetism, make it a prime option for any producer looking for a small town to set their story in. Below are just a few dreamy small towns that could fit the bill, or have fit the bill. 

1. Niantic

Location: Southeastern Connecticut 

Why It’s So Dreamy: This is one of the more underrated Connecticut waterfront small towns, with views of the Long Island Sound and an interesting stretch of boardwalk that curves alongside the beach. With small fishing boats bobbing in the water, local festivals that light up the restaurants, birdwatchers that gather in the parks bordering the ocean, a nearby state park and nature reserve, and a strollable small downtown with popular shops like The Book Barn, this is a relaxed and beautiful place to visit.

2. Woodstock

Location: Northeastern Connecticut on the Massachusetts border

Why It’s So Dreamy: Known best for its agrarian landscapes and fall apple picking, this is a quiet and gorgeous stretch of land with a fascinating blend of colonial and Gothic revival architecture. Ironically, by surface area, it would be considered one of the larger towns in Connecticut, but the population size refutes that, with rural farms and valleys full of forests taking up the space instead. As a result, the farm-to-table culture in the town is significant (especially when it comes to dairy), and many neighboring farms host holiday events.

3. Mystic

Location: Southeastern Connecticut on the coast

Why It’s So Dreamy: Yes, you’ve probably seen this town before. It was made famous by the Julia Roberts movie, Mystic Pizza, but has been a popular tourist destination for years before the movie, and retains this status even after. Set squarely on the Connecticut coast, this town is a slice of what true marine life looked like in New England over the years and has retained a historical, charmingly romantic feel to it. With the largest maritime museum in the country, visitors can walk through a historic village and interact with people in costume while exploring a working shipyard. 

4. Norfolk

Location: Northwestern Connecticut near the Massachusetts border

Why It’s So Dreamy: Known as the "Icebox of Connecticut" due to its high elevation and subsequent intense winters, this small town is very remote but is rather popular for winter sports. Keeping a peaceful, cozy vibe (especially in the winter), the downtown area features a village green and historic colonial homes, all set amid a hemlock forest. Other than winter sports and being a cold-weather hotspot, the town is also known for its maple syrup harvesting. 

5. Washington

Location: Western Connecticut 

Why It’s So Dreamy: Maybe this town doesn’t look familiar, but it certainly might feel familiar, as it was the inspiration for the town of Stars Hollow from "Gilmore Girls." Similar to the famous TV town, Washington is very walkable and well-maintained with a centralized town square, colonial-influenced architecture, lots of flowers and greenery that change with all four seasons, and an extremely involved community that often puts on events and hosts festivals. However, the town of Washington is more affluent than Stars Hollow and is manicured in a way that reflects that.  

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