Things to Do in Chester Connecticut

Discover the Charm of Chester Village

When you first arrive in Chester, Connecticut, one of the best places to start exploring is the charming Chester village.

This quaint village is known for its picturesque streets and unique shops.

You might begin your day by strolling down Main Street, where you will find a variety of boutiques and galleries.

Consider stepping into River Tavern for a locally-sourced meal that many locals rave about.

From farm-to-table dishes to delightful cocktails, it’s an experience that sits at the heart of Chester’s dining scene.

Take a Scenic Walk at the Cockaponset State Forest

Outdoor enthusiasts will love exploring Cockaponset State Forest.

This sprawling forest offers numerous trails that cater to different difficulty levels.

Whether you’re looking for a leisurely walk or a challenging hike, you’ll find it here.

The scenary is filled with diverse wildlife, making it a perfect spot for nature lovers.

Bring a picnic and enjoy a meal surrounded by the tranquility of nature.

It’s a great way to unwind and take in the peaceful environment.

Experience Art at the Chester Museum at The Mill

If you’re interested in art and history, the Chester Museum at The Mill is a must-visit.

This museum beautifully combines art exhibitions with historical displays.

The museum often features works from local artists, providing a glimpse into the creative talents of the area.

It’s an enriching experience that adds cultural depth to your visit.

The museum is often less crowded during weekdays, making it a good time to enjoy the exhibits at a leisurely pace.

Shop at the Chester Sunday Market

The Chester Sunday Market is the perfect place to immerse yourself in the local community.

Held every Sunday from June to October, this market features fresh produce, handmade crafts, and local delicacies.

It’s an excellent way to support local farmers and artisans.

You might find unique items that make great souvenirs or gifts.

The market can get quite busy, so arriving early might help you beat the crowd.

This market is a great opportunity to taste and purchase the best local products.

Enjoy a Day on the Connecticut River

The Connecticut River offers plenty of recreational opportunities.

Consider renting a kayak or a canoe to explore the river at your own pace.

You’ll find rental shops like Chester Point Marina that provide everything you need for a fun day on the river.

It’s said that hiring a kayak during sunset provides some of the most breathtaking views.

If you prefer staying on land, there are also guided river tours that offer historical insights and scenic views.

Dine on the Patio at The Wheatmarket

Dining at The Wheatmarket is a delightful experience.

This popular spot offers an array of delicious foods with a focus on locally-sourced ingredients.

With outdoor patio seating, it’s a perfect place to enjoy a meal while taking in the beautiful surroundings.

Their sandwiches and baked goods are particularly praised by locals and visitors alike.

It’s a friendly and relaxed environment that perfectly encapsulates the charm of Chester.

Stay at the Copper Beech Inn

If you’re planning an overnight stay, the Copper Beech Inn offers luxurious accommodations.

This historic inn combines classic elegance with modern amenities.

Each room is individually decorated, providing a unique and comfortable stay.

The inn also features an on-site restaurant known for its fine dining experience.

Many guests have praised the attentive service and the beautifully maintained grounds.

Staying here adds a touch of luxury to your Chester experience.

Explore Local Events and Festivals

Chester hosts several events and festivals throughout the year, making it an exciting place to visit any time.

The Chester Fair, held in August, is a traditional country fair with rides, games, and agricultural exhibits.

There are also art festivals, music events, and holiday celebrations that reflect the community’s vibrant culture.

Checking the local event calendar can help you plan your visit to coincide with one of these special events.

Participating in these events provides a deeper connection to the local culture and traditions.

Relax at Cedar Lake

For a relaxing day out, Cedar Lake is the perfect destination.

This freshwater lake is ideal for swimming, fishing, and picnicking.

There’s a sandy beach area where you can lay out a towel and soak in the sun.

The lake is especially popular in the summer months, so visiting early in the day might help you avoid the crowds.

It’s a great spot for families as there are designated swimming areas and life guards on duty.

Visit the 3 Legged Dog

The 3 Legged Dog is another unique spot in Chester that is well worth a visit.

This charming cafe and bakery is known for its cozy atmosphere and delicious pastries.

Whether you’re stopping in for a quick coffee or a leisurely brunch, you’ll be met with friendly service and delightful food.

Their homemade pies and cakes are particularly popular, often selling out by the afternoon.

It’s a great place to relax and enjoy some local flavor.

Catch a Show at the Norma Terris Theatre

The Norma Terris Theatre is a local gem for live entertainment.

Operated by the Goodspeed Musicals, the theatre showcases new and developing musicals.

Catching a show here provides a fantastic opportunity to see high-quality productions in a more intimate setting.

It’s a popular spot among both locals and visitors, so booking tickets in advance is recommended.

You might be lucky enough to see a pre-Broadway performance in this charming theatre.

Explore Nearby Areas for Additional Adventures

Chester’s location makes it easy to explore surrounding areas for even more activities.

Just a short drive away, you’ll find some of the best beaches in Rhode Island.

Or, you might want to check out some yoga retreats in the area for a more relaxing adventure.

There’s so much to see and do, both in Chester and in the surrounding regions.

Whether you’re interested in outdoor activities, cultural experiences, or simply relaxing, Chester, Connecticut has something for everyone.

Stroll Through the Gillette Castle State Park

A visit to Chester, Connecticut, would be incomplete without exploring the nearby Gillette Castle State Park.

This park is home to the unique Gillette Castle, once the residence of actor William Gillette.

The castle’s design is whimsical and offers a peek into Gillette’s creative mind.

Exploring the grounds, you’ll find trails and picnic areas that are perfect for a family day out or a romantic walk.

It’s often mentioned that the views of the Connecticut River from the castle are absolutely breathtaking.

Touring the castle itself provides fascinating insights into Gillette’s life and era.

Attend a Workshop at the Chester Library

The Chester Library isn’t just for borrowing books; it also hosts a variety of workshops and events.

From book clubs to crafting sessions, there are activities suitable for people of all ages.

These events are a great way to engage with the community and perhaps learn something new.

It’s worth checking their calendar to see what’s on during your visit.

The library’s tranquil atmosphere makes it a perfect place to spend a quiet afternoon.

Explore Eateries at Laurel Ridge Chocolate

For chocolate lovers, a stop at Laurel Ridge Chocolate is a must.

This local gem offers a delightful assortment of handmade chocolates that can satisfy any sweet tooth.

The owners are passionate about their craft, and it’s said that their truffles are particularly divine.

Alongside the chocolates, you’ll also find other treats and goodies that make perfect gifts.

The aromas inside the shop are enough to make anyone feel like they’ve stepped into a chocolate dream.

Join a Yoga Session at River Valley Yoga

If you’re looking to unwind and find some inner peace during your visit, consider joining a yoga session at River Valley Yoga.

Offering a range of classes suitable for all levels, this studio is a welcoming place to stretch and relax.

Many people say the instructors here are exceptionally skilled and create a calming environment.

After a session, you’ll likely feel rejuvenated and ready to explore more of what Chester has to offer.

It’s a wonderful way to balance physical activity with mental tranquility.

Check Out the Chester Historical Society

To delve deeper into the rich history of Chester, plan a visit to the Chester Historical Society.

This organization offers fascinating exhibits and archives that detail the town’s past.

From historical photographs to artifacts, you’ll gain a better appreciation of Chester’s heritage.

The dedicated volunteers are always happy to share stories and answer any questions.

It’s a meaningful experience that adds context to everything else you’ll see in town.

Sample Local Brews at Little House Brewing Company

Beer enthusiasts should make a stop at the Little House Brewing Company.

This small but vibrant brewery offers a rotating selection of craft beers that reflect the local flavor.

The atmosphere is relaxed and friendly, making it a great place to unwind with friends.

Many people recommend trying their seasonal brews for something unique.

It’s also worth noting their events and live music nights to add a bit of fun to your visit.

Visit the Shops at Maple and Main Gallery of Fine Art

For those who enjoy art, the Maple and Main Gallery of Fine Art is a must-visit.

This gallery showcases a diverse range of works from both established and emerging artists.

The pieces on display are always changing, providing a fresh experience each time you visit.

Art lovers often praise the curation and the friendly artists you can meet there.

It’s an inspiring way to spend your afternoon, especially if you have a passion for creativity.

Enjoy the Outdoors at Pattaconk Recreation Area

The Pattaconk Recreation Area is an excellent spot for outdoor activities.

From hiking and biking to fishing and swimming, there’s something for everyone.

The area is well-maintained and offers a beautiful setting for a variety of outdoor adventures.

During the warmer months, the swimming area is especially popular.

If you’re traveling with family, it’s a fantastic place to let the kids run around and enjoy nature.

Explore Indian River Marina

If you’re looking for more water-based activities, the Indian River Marina has a lot to offer.

Here you can rent boats, kayaks, and paddleboards to explore the water.

The marina is also a starting point for various guided tours, which can give you a new perspective on the local waterways.

It’s often mentioned that a sunset paddle here is a magical experience.

The staff at the marina are known for being helpful and knowledgeable, ensuring you have a great time on the water.

Attend a Performance at Chester Meeting House

The Chester Meeting House is a historic venue that hosts a variety of cultural events.

From theatre performances to musical concerts, there’s always something interesting happening here.

The intimate setting provides a unique experience compared to larger venues.

Check their schedule in advance to see if there’s a performance that interests you during your stay.

It’s said that the acoustics in this venue are top-notch, making every performance a treat for the ears.

Indulge at the Simon’s Marketplace

For a blend of delicious food and local products, Simon’s Marketplace is a go-to spot.

This charming market offers a range of fresh and prepared foods that are perfect for a picnic or a casual meal.

Their sandwiches and breakfast items come highly recommended by locals.

Take a moment to browse their selection of unique gifts and local products.

It’s a delightful place to grab a bite and perhaps find a souvenir to take home.

Savor a Meal at Otto Pizzeria

If you are a fan of Italian cuisine, a visit to Otto Pizzeria in Chester, Connecticut, is a must.

Otto is known for its authentic wood-fired pizzas and other delightful Italian dishes.

The menu features a variety of pizzas, pastas, and salads, ensuring there is something for everyone.

Many patrons rave about their Margherita pizza, which is made with fresh ingredients and cooked to perfection.

For a lighter option, consider trying their seasonal salads, which are often made with locally-sourced produce.

The friendly staff and cozy atmosphere make it a perfect spot for a casual meal with family or friends.

Take a Pottery Class at Lark

For a hands-on and creative activity, consider taking a pottery class at Lark.

This charming studio in Chester offers pottery classes for all skill levels.

The instructors are experienced and provide a welcoming environment for learning and creating.

It’s said that working with clay can be a therapeutic and satisfying experience.

You’ll leave with a unique handmade piece that you can cherish as a memory of your visit.

Be sure to book your class in advance, as spots can fill up quickly.

Explore the Chester/Hadlyme Ferry

A unique way to experience the Connecticut River is by taking the Chester/Hadlyme Ferry.

This historic ferry service has been operating since 1769 and offers a scenic crossing of the river.

The ferry ride provides beautiful views of the surrounding landscape and is especially picturesque during the fall foliage season.

It’s also a convenient way to access nearby attractions like the Gillette Castle State Park.

Operating hours vary seasonally, so it’s a good idea to check the schedule before you plan your trip.

Unwind at the Riverwind Inn Bed & Breakfast

For another charming accommodation option, consider staying at the Riverwind Inn Bed & Breakfast.

This historic inn offers a cozy and romantic setting with beautifully decorated rooms.

The innkeepers are known for their warm hospitality and delicious homemade breakfasts.

Each room has its own character, featuring antique furnishings and modern amenities.

The serene garden and lovely common areas provide perfect spots to relax and unwind.

Its central location makes it easy to explore all that Chester has to offer.

Shop for Antiques at Brown & Lum Antique Annex

If you love antiques, make sure to visit Brown & Lum Antique Annex.

This charming shop offers a wide variety of antique furniture, collectibles, and vintage items.

Browsing through their unique selection can feel like a treasure hunt with so many interesting finds.

The owners are knowledgeable and always happy to share the stories behind their items.

It’s a great place to find a special piece that adds a touch of history to your home.

Discover the Chester Green

At the heart of Chester lies the Chester Green, a beautiful public space that hosts various community events.

This scenic spot is a great place to relax, have a picnic, or simply enjoy the outdoors.

The green often hosts farmers markets, concerts, and cultural events, providing a lively atmosphere.

In the winter, the green is transformed into a charming holiday wonderland with festive decorations and activities.

It’s a perfect spot to soak in the local charm and community spirit.

Go Bird Watching at Selden Neck State Park

For nature enthusiasts, a visit to Selden Neck State Park is a real treat.

This park is accessible by boat and offers a pristine natural habitat for a variety of wildlife.

Bird watchers often flock here to observe the diverse bird species that call this area home.

The park also offers hiking trails and camping grounds for a more immersive experience.

It’s a quiet and peaceful retreat that’s perfect for connecting with nature.

Pick Your Own Produce at Scotts’ Farm & Greenhouses

An enjoyable and family-friendly activity is visiting Scotts’ Farm & Greenhouses for some pick-your-own produce fun.

This farm offers a seasonal selection of fresh fruits, vegetables, and flowers that you can pick yourself.

It’s a wonderful way to spend a sunny day, enjoying the fresh air and beautiful farm scenery.

The farm also has a market where you can purchase fresh, locally-grown produce and homemade goods.

Children especially love participating in the picking process, making it a great outing for the whole family.

Sip Coffee at the Grano Arso’s Café

For a relaxing coffee break, head over to Grano Arso’s Café.

This café is loved by locals for its artisanal coffee and cozy atmosphere.

It’s an ideal spot to recharge after a day of exploring Chester.

They offer a selection of pastries and light snacks to complement your coffee.

The friendly baristas are always happy to recommend their favorite brews or make a custom drink just for you.

Embark on a Historical Adventure with Essex Steam Train & Riverboat

A short drive from Chester will take you to the Essex Steam Train & Riverboat for a unique historical adventure.

This attraction offers a scenic train ride combined with a riverboat cruise along the Connecticut River.

It’s a fun and educational experience that the whole family can enjoy.

The vintage steam train and riverboat provide spectacular views of the river valley and its historic landmarks.

It’s often said that the fall foliage rides offer some of the most breathtaking scenery.

Booking in advance is recommended, especially during peak seasons.

Indulge in Fine Wine at the Priam Vineyards

For wine lovers, a visit to Priam Vineyards, located not far from Chester, is highly recommended.

This award-winning winery offers wine tastings and scenic views of the vineyard.

The friendly staff are knowledgeable and eager to share their passion for their wines.

You’ll find a variety of wines to sample, from crisp whites to robust reds.

It’s a relaxing way to spend an afternoon, sipping wine and taking in the beautiful surroundings.

Many visitors comment on the serene and picturesque setting that adds to the overall experience.

Explore Chester’s Surrounding Towns

If you have extra time during your visit, consider exploring Chester’s neighboring towns for even more adventures.

Nearby Lyme offers some of the best trails in Rhode Island and is perfect for hiking enthusiasts.

For those interested in yoga retreats, the region surrounding Chester provides various holistic health options.

Additionally, summer beach destinations are just a short drive away, ideal for a relaxing day by the ocean.

Each surrounding town has its unique charm and attractions, making it worth venturing out to explore.

Final Thoughts

Chester, Connecticut, is a town rich in charm and activities, ensuring there’s something for everyone to enjoy.

From scenic nature walks and historical sites to vibrant local markets and fine dining, your visit will be filled with memorable experiences.

Whether you’re spending a day or a weekend, you’ll find that Chester offers a welcoming and delightful escape from the everyday hustle and bustle.

We hope you find these suggestions helpful and enjoy all that Chester has to offer.