The Unassuming Town Of Chester, Connecticut Is One Of America's Best Hidden Gems For A Weekend Getaway
By Lisa Sammons|Updated on January 11, 2024(Originally published January 09, 2023)
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Lisa Sammons
Author
Lisa loves animals and has dogs, rats, cats, guinea pigs, and snakes. She is passionate about animal rescue and live music - traveling across the country to see a favorite band is a pretty regular occurrence! Being out hiking in the woods enjoying the scenery with her beloved dogs is another favorite hobby, and also checking out the Pokemon Go scene in whatever city she happens to be in at any given time (coffee and dog leash in hand). You can reach Lisa at lsammons@onlyinyourstate.com
The Nutmeg State may get a bad rap from outsiders – we’re often thought of as boring and filled with lots of businesses and traffic, but not much else. Even so, if you’ve spent any time here, you know there are tons of great weekend getaways in Connecticut. From our luxurious beaches and big-city attractions, there’s a lot to love here, but if you ask us, the CT small towns are some of the best in the country! One of the most unassuming small towns in CT that makes for a wonderful weekend trip is Chester. This little town has a population of just under 4,000, but it has a surprising array of attractions. It’s also a great home base for several adventures in this area of the state, plus it’s filled with natural beauty and quaint New England charm that looks straight off of a postcard.
Chester's adorable downtown area feels like a throwback to old New England. You'll find lots of 19th century-era architecture here. Between the boutique shops and the locally-owned restaurants, there's tons to love here.
As you meander through the town's winding streets, you'll find so much beautiful architecture that makes this one of the best small towns in Connecticut.
The sprawling Cockaponset State Forest encompasses more than 17,000 acres. The preserve spans through several towns, including Chester. For more information about the great trails at Cockaponset State Forest, check out our friends at Alltrails - this place is a hiker's paradise!
If you're a fan of musical theater, you won't want to miss a visit to the Terris Theatre. This place has won two Tony Awards, and hosts fun events throughout the year.
The Terris Theatre, 33 N Main St, Chester, CT 06412, USA
This alpaca farm Chakana Sky Alpacas offers seasonally-available one-hour tours by appointment only, so book ahead on the farm's website. There's also a farm store where you can purchase great products made from the wool here.
One of our favorite things about Chester is that it's a great launching point for other adventures in Connecticut. The town is home to the second-oldest continuously-operating ferry in all of Connecticut.
Chester-Hadlyme Ferry (West Side Landing), 99 Ferry Rd, Chester, CT 06412, USA
The ferry, which operates from spring to fall, will take you to the Haddam side of the Connecticut River, where you can visit the magnificent Gillette Castle State Park. This is one of the most beautiful state parks in Connecticut and it's definitely worth a visit.
If you decide that you'd like to stay in the area the entire weekend, it doesn't get much better than a stay at the Boardman House in nearby East Haddam.
Boardman House, 8 Norwich Rd, East Haddam, CT 06423, USA
Essex was actually officially named the country's coolest small town.
What are some more great weekend getaways in Connecticut?
From our CT small towns to our big cities, there are enough great weekend getaways in Connecticut to keep you busy for a year (and then some). Here are some we recommend:
