Travel Guide to Chester, CT, and Its Best Attractions

Discover these five unique attractions in Chester, Connecticut.

Hopper Editors - Oct. 26, 2017

Chester, Connecticut, is one of those towns that would make travelers wish it were autumn all year round, if the other three seasons in this cozy little village weren't so stunning. For a day away and a dose of small-town friendliness, Chester is the perfect little break. Here, travelers can get all the important amenities, like a thriving arts culture, fine dining, and excellent shopping, but without the bitter rush of traffic and menacing grey buildings. Those looking to stay longer in the region will find plenty to do elsewhere in the Connecticut River Valley, as well.

All about Chester at the Museum At The Mill

Photo by Jay McAnally via Flickr

A refurbished mid-1800s mill site, the Chester Museum contains everything there is to know about the history of this "prototypical New England small town". From exhibits about transportation in Chester to galleries of recovered photographs reflecting over a century of small-town life, the museum allows you to literally step into history and learn all about it.

Dramatic wonderment at The William Gillette Castle

Meticulously designed by William Gillette himself, the curious castle with its ornate sliding locks and door knobs sits on top of the hill that is part of what is called the William Gillette Castle State Park. The former estate of the great stage actor is now open to visitors and wanderers alike, and is one of the most scenic discoveries in the Chester area.

Unpretentious French food at Restaurant L&E

Photo via their official FB page

For a romantic restaurant, look no further than Restaurant L&E, a cozy French bistro in downtown Chester. This local favorite has expanded over the years to cover both floors of their adorable blue and red storefront, and their menu will be sure to trigger premature salivation with items like Pan Seared Atlantic Skate Wings with Brown Butter with Pancetta and Leek Confit.

River Tavern Restaurant proves that you don't have to go far for good food

Photo by Alex Bajuniemi via Flickr

Locals flock to the River Tavern Restaurant for their classic but modern dishes like sautéd fresh shrimp & squid with crispy polenta. Locals also flock to the River Tavern Restaurant because they know it's all local – the chefs work directly with local farms, fish in the nearby rivers, and shop the markets. In fact, the restaurant throws regular Dinners at the Farm, held on local farms to celebrate local agriculture.

Norma Terris Theatre might as well be called Little Broadway

Photo via their official FB page

Walking around the charming village of Chester, with its quaint antique shops, boutiques and cozy restaurants, it's easy to miss the Norma Terris Theatre. However, in this little playhouse, the stuff of Broadway is on the stage nightly – new musicals often start their rounds in Norma Terris, and sometimes they make it to the big stage.

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