We’re well-known for our charming small towns in Connecticut – we have countless examples of the quintessential old New England town, you know the kind, with adorable Main Streets and local shops galore. One of our favorites is Deep River, which is named for an offshoot of the nearby Connecticut River. The mighty waterway is not only the longest river in New England, measuring 410 miles, but also pretty deep (131 feet at its deepest point). The town of Deep River is in Middlesex County and has a population of around 5,000. It’s not quite as well-known as nearby Essex, but it’s a lovely spot and definitely worthy of a day trip!

Deep River, Connecticut is in the Tri-Town area, made up of Deep River, Essex, and Chester, CT. Deep River is about 14 square miles.
Unknown author / Wikimedia Commons
This area was one of the first to be settled in Connecticut, so as you can imagine, there are lots of historical attractions to explore.
Town of Deep River/Facebook
The Deep River Historical Society maintains several historic homes that are open for tours and also hosts regular events and exhibits.
Deep River Historical Society/Google Maps

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You'll also find tons of charming stores, like the delightful Anchor and Compass, a wonderful menswear store.
Anchor & Compass/Facebook
Deep River is located right on the Connecticut River, hence its name.
Deep River
Thanks to the close proximity to the river, you can find a number of water attractions here, including rides on the Becky Thatcher Riverboat.
Deep River
Whether you're visiting for the historical attractions, the shopping, or the natural surroundings, you're sure to find that Deep River is one of the most charming small towns in Connecticut.
Deep River

For more information about this delightful little town, check out the Deep River, CT website.

Have you ever visited Deep River, one of the most charming small towns in Connecticut? Share your experiences in the comments! And if you’re looking for a place to stay in town, book a stay at one of the available vacation rentals listed on Vrbo.

If you want to explore Northwest Connecticut, take a look at this video from OnlyInYourState, and don’t forget to subscribe to the YouTube Channel!:

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Deep River, CT, USA