There's something about rural New England that's utterly intoxicating. The small towns here ooze historic charm. Delicious little eateries; curated galleries and boutiques; cozy B&Bs and inns; quiet forests and farmland and more add flavor to these quaint settlements. Chester, Connecticut is a picture-perfect example of a New England town. Right between Boston and NYC on the rolling, hilly banks of the Connecticut River, Chester is an artsy community that takes pride in its rich history (it was settled in 1692!) and lush farm-filled landscape surrounding the town. It's the perfect escape from city living, since time here moves at a captivatingly slow pace. A long weekend here exploring the countryside is sure to be a delightful experience.
Chester's population hasn't cracked 4,000, but it's still got plenty of shops, restaurants, and attractions, making it a great destination for a quiet weekend. It's attracted artists, chefs, antique collectors, and more, so the downtown section has lots to see and do. Plus, since the town has seen quite a bit of history, there are some pretty special attractions right nearby.
You couldn't ask for a better location for a history museum then Chester's old 1860s-era mill. It overlooks a waterfall and embodies the perfect quaint vibe that makes the rest of the town so special. The first floor features a special exhibit that rotates annually, while the second floor houses their in-depth exhibit on Chester's 300-year history. It houses the town's oldest artifacts: two 285-year-old millstones from a historic grist mill that operated between 1740 and 1810.
There are a few galleries in Chester, unusual for such a small town, but few have the atmosphere of Maple and Main. It's located in an 18th-century ship's chandlery, and it rotates its exhibitions of all original art every two months. Opening receptions, lessons and classes, and more mean there's usually something happening and engaging the community here. Plus, you can see tons of art inspired by Chester!
When it comes to dining, you have tons of different options. One local favorite is the River Tavern. They serve creative and fresh food in a colorful and comfy environment. They have a bar with craft cocktails, and their lunch and dinner menus rotate seasonally to feature local ingredients. Handmade pasta, fresh seafood, and a killer burger plate are highlights here. They also occasionally host an event called "Dinner at the Farm", where they take over a local farm to host a multi-course feast prepared on the back of their vintage cook truck–a 1955 Ford F-600- from ingredients harvested that day.
For a more casual lunch or breakfast, head to Simon's Marketplace. Fresh salads, soups, wraps, bread, sandwiches, sides, hot dishes, breakfasts, and more make up a menu of delicious grub that rotates daily. It's also got gifts and special little things for sale inside as well, so even if you just stop by for a coffee or iced tea and just browse, you're sure to be charmed by this little local favorite.
For a taste of that serene New England woodland, head to Pattaconk Recreation Area. It's in Cockaponset State Forest, Connecticut's second-largest state forest, so there's plenty of room for you to get a little lost and do some exploring. It's also on a reservoir, so there are opportunities for fishing and boating as well.
Just outside Chester, you'll find a cozy B&B, the Riverwind Inn Bed and Breakfast. Located in a restored 19th-century building, it features great accommodations like private bathrooms, period antique furnishings, and a killer country-style breakfast each morning. At night, wind down with some tea in front of the 12-foot-long Rumford fireplace, which just so happens to be made of stone from the original foundation.
Make a point to take a ride on the historic Chester-Hadlyme Ferry. It's been bringing people across the Connecticut River since 1769, and it played a big role in moving supplies during the American Revolution. Originally, the boat was maneuvered across the river using long poles, but today, you'll get across on the Selden III, a 1949-era open craft. It's open seasonally, from late April until November, and fits 8 or 9 cars and about 49 passengers. And once you cross the river, you can make your way to one of the state's craziest and coolest state parks, Gillette Castle State Park. While crossing the river, the castle is in full view, in all its majesty sitting atop the cliffs!
It's not very often that you get to tour a dead, eccentric, rich dude's castle, so the chance to explore a building that's basically like a mansion from "Scooby Doo" is pretty awesome. At Gillette Castle State Park, you're invited right inside the medieval-style castle that was once home to a famous (and slightly odd, but in the best way possible) stage actor.
The castle was built by William Gillette, best know for his theatrical turn as Sherlock Holmes, in 1914. And, like every eccentric rich person, he designed it himself and added some...unusual features. You know, like a system of mirrors that allowed him to keep an eye on the rest of the house (and any guests staying there) from the master bedroom, a unique system of doorknobs and locks, and a train that circles the castle grounds. There are 47 doors in the building, and no two are alike. Other touches include built-in couches on moveable tracks and wooden light switches. He even designed the aerial tramway that brought the building materials to the property himself. Gillette also had a special name for his regal estate: he called it "The Seventh Sister" because it was built on the last hill in a chain known locally as The Seven Sisters.
Gillette died in 1937, leaving behind no wife or children (his wife had died in the 1880s and he never remarried) to whom he could bequeath his estate. In his will, he only specified that it should not go to any "blithering sap-head who has no conception of where he is or with what surrounded", which is maybe the coolest thing I've ever seen written in a will, ever. Whether he considered the government "blithering sap-heads" or not, the state of Connecticut took over the property and turned it into a state park in 1943-- at the very least, they seemed to understand Gillette's appreciation for the place.
In 1999, Gillette Castle itself underwent a 4-year, 11 million dollar restoration that added a museum and theater space to the building, as well as a picnic area and hiking trails in the park. The trails mostly follow the railroad tracks, with trestles and tunnels, and past the railroad station.