Village and Castle: A Day Trip to Chester, CT
Nestled snugly in the heart of the Constitution State, Chester, Connecticut, is the quintessential embodiment of New England charm. This picturesque small town, with its idyllic riverside setting and historic character, beckons travelers seeking a tranquil escape from the hustle and bustle of city life.
As you approach Chester, you'll immediately notice the postcard-perfect scenery that surrounds it. The town is cocooned by lush forests, and the gentle waters of the Connecticut River meander through its landscape, creating a serene and timeless ambiance. Chester's beauty is not only a treat for the eyes but also a soothing balm for the soul.
The town's storybook appearance is further enhanced by its charming, well-preserved architecture. Stroll along the cobblestone streets, and you'll encounter historic buildings adorned with flowering window boxes, inviting you to explore their rich past. Each corner seems frozen in time, evoking a sense of nostalgia that's simply enchanting.
But Chester isn't just a visual delight; it's a town that engages all your senses. The scent of freshly baked bread wafts from artisanal bakeries, enticing you to savor a warm loaf. The gentle rustling of leaves overhead and the babbling of the river provide a soothing backdrop to your visit. And the friendly smiles of the townsfolk make you feel like you've found a second home.
In this blog post, we'll take you on a journey through Chester's hidden gems, scenic vistas, mouthwatering cuisine, and intriguing history. So, join us as we explore this hidden gem by the river, where time seems to slow down, and the beauty of Connecticut shines through in every cobblestone and corner. Welcome to Chester!
QUICK DETAILS:
Time commitment: Full-Day
Trip Vibe/ Aesthetic: Quaint Village Life & River Scenes
Where to Park:
Parking for the Downtown Business District is available along Main Street and in 3 lots off Main Street that are easily accessible on foot. Follow the signage to park and then follow the new sidewalks right into downtown! There is one handicap parking space on Main Street in front of the Pattaconk Restaurant. MAP HERE
Stroller friendly: Yes
Dog Friendly: Yes but check with restaurants first.
Family friendly: Yes
Best weather for this trip: Sunny days, not too hot.
Best season for this trip: Year-Round
CHESTER DAY TRIP PHOTO GALLERY:
*Photo Gallery with descriptions of locations located at the bottom of this post…since nothing is more frustrating than being unable to find that insta-worthy spot once you arrive to town.
A Day Trip to Chester, CT Itinerary
Get the printable itinerary here.
Morning:
9:00 AM - Start Your Day at Simon's Marketplace
Address: 17 Main St, Chester, CT 06412
Begin your day with a hearty breakfast or a freshly brewed cup of coffee at Simon's Marketplace, a cozy spot in the heart of Chester.
WEBSITE & MENU:
10:00 AM - Explore Chester Village Shops
Stroll through the charming streets of Chester Village, exploring the unique boutiques, galleries, and antique shops.
Address: Various shops along Main Street, Chester, CT 06412
11:30 AM - Visit the Chester Museum at The Mill
Discover the history of Chester at the Chester Museum at The Mill, housed in a beautifully restored 19th-century mill.
Address: 9 W Main St, Chester, CT 06412
WEBSITE:
12:30 PM - Lunch at River Tavern
Enjoy a delicious farm-to-table lunch at River Tavern, known for its seasonal menu and inviting atmosphere.
Address: 23 Main St, Chester, CT 06412
WEBSITE & MENU:
Afternoon:
2:00 PM - Chester-Hadlyme Ferry Ride
Experience a scenic ferry ride across the Connecticut River on the Chester-Hadlyme Ferry.
Address (Ferry Landing): Ferry Rd, Chester, CT 06412
3:00 PM - Explore Gillette Castle State Park
Visit Gillette Castle State Park, the former home of actor William Gillette, and explore the castle's unique architecture and scenic trails.
Address: 67 River Rd, East Haddam, CT 06423
WEBSITE:
5:00 PM - Dinner at The Brushmill by the Waterfall
Enjoy a picturesque dinner by the waterfall at The Brushmill, offering a diverse menu in a charming setting.
Address: 129 W Main St, Chester, CT 06412
WEBSITE & MENU:
Evening:
7:00 PM - Chester Village Lantern Tour (Seasonal)
If available (seasonal), take a lantern tour of Chester Village to learn about its history and ghostly tales.
Address (Tour Starting Point): Various locations in Chester, CT 06412
OR
7:00 PM - Evening Stroll by the Chester Creek
Enjoy a leisurely evening stroll along the scenic Chester Creek, located near the village center.
8:00 PM - Dessert at Honeycone Craft Ice Cream
Satisfy your sweet tooth with delectable ice cream. “Sourced Locally, Made Daily with Love”
Address: 29 Main St, Chester, CT 06412
WEBSITE & MENU:
9:00 PM - End of Your Day in Chester, CT
As the day comes to a close, head back to your accommodations or continue to explore the serene charm of Chester at your own pace.
*Please note that this itinerary provides a mix of indoor and outdoor activities, making it suitable for various interests and seasons. Make sure to check the opening hours and availability of seasonal activities in advance. Enjoy your day trip to Chester, Connecticut!
FAQ’s
Where to Park:
Parking for the Downtown Village of Chester is available along Main Street and in 3 lots off Main Street that are easily accessible on foot. Follow the signage to park and then follow the new sidewalks right into downtown! There is one handicap parking space on Main Street in front of the Pattaconk Restaurant. MAP HERE
