Chester, Connecticut is a hidden gem in the heart of New England. This charming small town offers a perfect escape from the hustle and bustle of city life.
Nestled in the scenic Connecticut River Valley, Chester boasts a vibrant community spirit and picturesque views that will captivate you.
Chester’s Main Street is a treasure trove of unique shops, art galleries, and cozy cafes, making it an ideal destination for a day trip or weekend getaway. You’ll find yourself strolling along cobblestone streets, admiring historic buildings, and soaking in the small-town charm.
The Chester Rotary and volunteer fire department contribute to the strong sense of community that you’ll feel as soon as you arrive.
Whether you’re looking for outdoor adventures in nearby state forests or a relaxing afternoon exploring local artisan shops, Chester has something for everyone.
Its blend of natural beauty, rich history, and friendly atmosphere makes it a must-visit destination in Connecticut.
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How to Get to Chester
Chester is a charming town in Middlesex County, Connecticut. You have several options to reach this picturesque destination.
By car, Chester is easily accessible. It’s about a 2-hour drive from New York City. Take I-95 North, then merge onto CT-9 North. Follow signs to Chester.
If you prefer public transportation, trains are available. Take Amtrak to Old Saybrook station, then catch a local bus or taxi to Chester. The journey is scenic and relaxing.
For those flying in, the nearest major airport is Bradley International Airport in Hartford. From there, you can rent a car or take a shuttle to Chester.
Once in Chester, you’ll find the town is walkable. Many attractions are within easy reach on foot.
For exploring the surrounding area, consider renting a bike or car.
Remember to check travel times and book in advance, especially during peak seasons. Chester’s charm awaits you, no matter how you choose to arrive.
What to See in Chester
Chester is a charming town packed with attractions. You’ll find plenty to see and do here.
Main Street is the heart of Chester. It’s lined with unique boutiques, art galleries, and restaurants. Take a stroll and soak in the small-town atmosphere.
Art lovers will enjoy the Chester Gallery. It showcases local and regional artists’ work.
For outdoor enthusiasts, Cockaponset State Forest offers hiking trails and fishing spots. Cedar Lake is perfect for swimming on hot summer days.
Don’t miss the Gillette Castle State Park. This medieval-style castle offers stunning views of the Connecticut River.
Food is a big draw in Chester. Try River Tavern for fine dining or Little House Brewing for craft beers. Grano Arso serves delicious Italian cuisine with seasonal flavors.
The Chester-Hadlyme Ferry is a fun way to cross the Connecticut River. It’s been operating since 1769.
Special events enliven the town year-round. Don’t miss First Friday art walks, the Sunday Market, or the annual Lobster Fest.
Chester is also close to the Goodspeed Opera House, a renowned theater just a short drive away.
Where to Stay in Chester
If you know when you are planning to go but haven’t decided on accommodation, then use the map below to get an idea of which properties are available and to compare prices during the period you wish to travel.
Enter your proposed dates and use the ‘+’ to zoom in on a location and reveal more properties. Click on the price above a property to see more information.
(Please note that this selection will also include some vacation homes, AirBnBs, and VRBOs for those who are interested in that form of accommodation!)
History of Chester
Chester, Connecticut has a rich past dating back to the 17th century. The area was first settled in 1692 as part of Saybrook Colony. It became its own town in 1836.
In its early days, Chester was known for shipbuilding and milling. The Connecticut River played a key role in the town’s growth, serving as a vital transportation route.
You’ll find many well-preserved historic buildings as you explore Chester. The Chester Historical Society works hard to maintain the town’s heritage.
One notable structure is the Boardman House. Built in 1780, it’s a fine example of colonial architecture. You can admire its classic New England style as you stroll through town.
Chester’s industrial roots are still visible today. Old mill buildings and riverside warehouses remind you of the town’s busy past.
As you walk Chester’s charming streets, you’ll feel like you’ve stepped back in time. The town has kept its quintessential New England village charm while adapting to modern times.
Towns Near Chester
Chester sits in a prime location surrounded by charming New England towns. You’ll find plenty to explore within a short drive.
Essex is just 4 miles away. This picturesque village offers scenic river views and a quaint Main Street lined with shops and restaurants.
Deep River, only 3 miles from Chester, boasts a rich history and beautiful parks along the Connecticut River.
For beach lovers, Old Saybrook is a must-visit. About 10 miles from Chester, it features lovely beaches and a bustling downtown.
East Haddam lies 7 miles north. Here you can catch a show at the famous Goodspeed Opera House.
Haddam, just 5 miles away, offers scenic river views and hiking trails.
Westbrook, 12 miles south, provides more beach options and coastal charm.
Old Lyme, about 15 miles away, is known for its art museums and galleries.
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