Guidebook for Chester
Food Scene
Excellent breakfast. Located in the heart of downtown, near the other great restaurants. Cash only!
7 locals recommend
The Villager
13 Main StExcellent breakfast. Located in the heart of downtown, near the other great restaurants. Cash only!
Brushmill By The Waterfall
129 W Main StClose by, good food, decent bar.
The Whole Enchilada
24 Boston Post RdThey do the best quesadillas (pizza style) on the shoreline.
Mindy K Deli Catering LLC
1610 Boston Post RdGreat mix of American and traditional Chinese food.
Drinks & Nightlife
Pattaconk 1850 Bar & Grille
33 Main StJust a good bar.
Parks & Nature
Huge range of varied trails that extend for miles and miles between three nearby towns.
9 locals recommend
Cockaponset State Forest
Cedar Lake RoadHuge range of varied trails that extend for miles and miles between three nearby towns.
Great place to go swimming and hike the trails. They occasionally charge for parking in the summer.
Pattaconk Reservoir
Great place to go swimming and hike the trails. They occasionally charge for parking in the summer.
Sightseeing
Local historical society. Please call in advance to book a reservation with them!
Chester Historical Society
9 W Main StLocal historical society. Please call in advance to book a reservation with them!
Beautiful state park with one of the few castles in Connecticut. Entrance to the park is free, and a paid tour of the castle is available.
24 locals recommend
Gillette Castle State Park
Gillette Castle State ParkBeautiful state park with one of the few castles in Connecticut. Entrance to the park is free, and a paid tour of the castle is available.
Essentials
Super Stop & Shop
665 Boston Post RdWalgreens Pharmacy
180 Main StNearest chain pharmacy
Adams Hometown Market
193 Main StNearest grocery store.
Getting Around
Enterprise Rent-A-Car
360 Boston Post RdOld Saybrook Station
455 Boston Post RdArts & Culture
Small community theatre associated with the nearby Goodspeed Opera House.
6 locals recommend
The Terris Theatre
33 N Main StSmall community theatre associated with the nearby Goodspeed Opera House.
This famous opera house offers off broadway plays and has been a cultural mainstay of the area for generations.
57 locals recommend
Goodspeed Opera House
6 Main StThis famous opera house offers off broadway plays and has been a cultural mainstay of the area for generations.