Things to Do in Chester Massachusetts
Updated June 27, 2024 at 3:11 pm
Discover the charm of Chester, Massachusetts with our guide to the best local attractions and activities, from scenic hikes and historic sites to culinary delights and cultural experiences.

Exploring the Outdoors in Chester, Massachusetts
If you love nature, Chester, Massachusetts, is the perfect place for you.
One of the must-visit spots is the Chester-Blandford State Forest.
This state park offers an array of activities like hiking, picnicking, and even cross-country skiing in winter.
The Sanderson Brook Falls is a highlight, especially during the early spring when the waterfall is at its most vigorous.
Visiting Local Historic Sites
History buffs will find plenty to discover in Chester.
The Chester Railway Station is a historic gem worth exploring.
This 19th-century station gives you a glimpse into the rich history of the railway industry in the area.
Be sure to check their open hours as they might change with the seasons.
People often say it’s best to visit during the summer when the tours are more frequent.
The Annual Chester on Track Festival
If you’re in town in May, don’t miss the Chester on Track Festival.
This event celebrates the town’s railway heritage and features train rides, parades, and live music.
The festival is kid-friendly, so bring the whole family for a day of fun.
Dining at Local Restaurants
Eating local is a great way to experience a new place.
For a cozy diner experience, head over to Classic Pizza & Family Restaurant.
Their menu ranges from classic pizzas to delicious pasta dishes.
Don’t forget to try their garlic knots, people rave about them!
If you’re looking for something a bit more upscale, The Chester Common Table offers a farm-to-table menu that’s simply exquisite.
Reservations are recommended, especially during weekends, as this hotspot can get quite busy.
Shopping at Local Stores
There’s something quaint and charming about local shopping in Chester.
The Chester Village Market is perfect for picking up some fresh produce or unique local products.
For book lovers, the Chester Railway Station & Museum Bookstore offers a variety of books focused on local history and railways.
You can also find railroad-themed toys that make for excellent souvenirs.
Enjoying Family Time at Great Outdoor Spots
Got kids? Chester has you covered.
The Littleville Lake Recreation Area is an excellent spot for family outings.
You can enjoy activities like fishing, boating, and picnicking.
This is an ideal place for some downtime as it’s often not crowded.
Heading to the Chester Theater Company
Don’t pass up the opportunity to see a show at the Chester Theater Company.
This local theater showcases a variety of plays from contemporary dramas to classic adaptations.
Check their calendar for current performances and get your tickets early, as shows can sell out quickly.
Thrilling Activities at Becket Quarry
A short drive from Chester is the Becket Quarry, perfect for adventure seekers.
You can explore the historical quarry and learn about its past through informative plaques.
For a real adrenaline rush, the area also offers rock climbing opportunities.
Relaxing at Jacob’s Pillow Dance Festival
Jacob’s Pillow Dance Festival, located near Chester, is another cultural stop you must not miss.
Held annually, this festival features a variety of dance performances and attracts talents from around the world.
You can even participate in dance workshops to get a feel of the art form.
Tickets can be booked online, making it easy to secure your spot.
Participating in Local Events
The community spirit is vibrant in Chester, with several local events happening throughout the year.
From farmer’s markets to community fairs, there’s always something to look forward to.
Visiting these events not only supports local businesses, but also allows you to interact with locals and truly understand the Chester lifestyle.
Finding Accommodations
Depending on your preference, Chester offers a range of places to stay.
For a cozy and intimate stay, local bed and breakfasts like the Cobble Mountain Lodge provide a homely experience.
These spots get great reviews for their hospitality and the home-cooked breakfast offerings.
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If you prefer more mainstream accommodation, hotels and motels are available in the surrounding areas as well.
Exploring Nature at Glendale Falls
Nature lovers visiting Chester, Massachusetts, should definitely take a trip to Glendale Falls.
It’s one of the highest waterfalls in Massachusetts, offering a spectacular sight, especially after a rainstorm.
The surrounding area provides excellent hiking trails where you can enjoy the serene beauty of the forest.
This spot is perfect for a relaxed day out, whether you prefer hiking, having a picnic, or just soaking in the natural beauty.
Many locals and visitors recommend visiting during the spring and summer months to see the waterfall at its fullest.
Taking a Scenic Drive along Jacob’s Ladder Scenic Byway
If you love scenic drives, the Jacob’s Ladder Scenic Byway is a must-do.
Stretching from Russell to Lee, this drive offers breathtaking views of the Berkshire Hills.
In the fall, the foliage is particularly stunning, making it a perfect time for a leisurely drive.
There are several spots along the route where you can pull over and take in the views or have a picnic.
Don’t forget to bring your camera; the picturesque landscapes are an Instagrammer’s dream.
Exploring Hampden Park
Hampden Park in Chester offers a great spot for various outdoor activities.
Families can enjoy the playground, while sports enthusiasts might appreciate the open fields for games.
It’s also a fantastic spot for birdwatching, with many species frequenting the area.
The park is well-maintained and has several picnic areas, perfect for a family day out.
Visiting on weekdays can be more peaceful as weekends can get a bit crowded.
Sampling Local Wines at Black Birch Vineyard
Wine enthusiasts will love a trip to Black Birch Vineyard.
Located a short drive from Chester, this vineyard offers tastings of locally produced wines.
The tasting room provides a cozy atmosphere where you can sample different varietals and learn about the winemaking process.
Visitors often mention the friendly staff and the beautiful scenery surrounding the vineyard.
It’s best to check their schedule as they sometimes host special events like wine and cheese pairings.
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Relaxing at Gateway Farm Alpacas
For something truly unique, why not visit Gateway Farm Alpacas?
This farm offers tours where you can meet and interact with their friendly alpacas.
It’s a fun and educational experience, especially for children who can learn about these fascinating animals.
You can even purchase alpaca wool products straight from the farm.
The wool is known for being incredibly soft and warm, perfect for winter clothing.
Shopping at Local Artisanal Stores
Chester boasts several charming artisanal stores where you can find unique, handmade items.
One such place is Chester’s Art Studio and Gallery, which showcases works from local artists.
Here you can purchase paintings, sculptures, and other forms of art.
Additionally, many stores offer locals crafts like handmade jewelry and pottery.
These make for excellent souvenirs or gifts and offer a piece of Chester to take home with you.
Fishing and Boating at Hampton Ponds State Park
About a 30-minute drive from Chester, Hampton Ponds State Park is an excellent spot for fishing and boating.
The park has several ponds stocked with a variety of fish species, making it a popular spot for anglers.
If you prefer boating, there are facilities to launch your own boat or rent one on-site.
The park also offers swimming areas and picnic spots, making it a great place for a family outing.
Weekdays are generally quieter, while weekends can get busy, especially during the summer months.
Visiting Chesterfield Gorge
A visit to Chesterfield Gorge is a must for adventure lovers.
This natural gorge offers stunning views and opportunities for hiking.
The trails are well-marked and range from easy to moderate difficulty, suitable for all fitness levels.
The gorge is particularly beautiful in the fall when the leaves change colors.
If you’re a photography enthusiast, this spot will provide endless opportunities for capturing nature at its best.
Browsing Books at the Chester Public Library
Book lovers will find a haven at the Chester Public Library.
This quaint library offers a good selection of books, including many on local history.
It’s a peaceful place to spend an afternoon reading or researching.
The library often hosts events like book readings and children’s story time, making it a great community hub.
Check their event calendar online to find out what’s happening during your visit.
Checking Out Local Coffee Shops
If you need a caffeine boost, Chester has several cozy coffee shops to choose from.
The Daily Grind is a popular spot, known for its excellent coffees and homemade pastries.
It’s the perfect place to start your day or catch up with friends.
The atmosphere is inviting, and the baristas are always friendly and helpful.
People often recommend trying their seasonal specials, which are always a hit.
Another coffee spot worth mentioning is CafeCito Chester, which offers a cozy setting with locally sourced ingredients.
They also serve light meals and have a great selection of teas for non-coffee drinkers.
This place often gets busy during weekends, so visiting during weekdays can provide a more relaxed experience.
For more coffee shop recommendations, check outthese excellent spots around Rhode Island.
Hiking in the Surrounding Mountains
Chester is nestled in an area with access to numerous hiking trails in the surrounding mountains.
One highly recommended trail is the Keystone Arches Bridges Trail.
This trail takes you through lush forests and over historic stone railway bridges, offering both natural beauty and a touch of history.
Another favorite is the Mohawk Trail, which provides stunning views of the Berkshires.
Popular among both casual hikers and seasoned trekkers, these trails are perfect year-round but offer spectacular views in the fall.
Make sure to bring plenty of water and wear proper hiking shoes for a comfortable experience.
Thinking about venturing further for hiking? Check out thebest trails for hiking aficionados in Rhode Island.
Exploring the Secret Gardens of Chester
There’s something magical about stumbling upon hidden gardens, and Chester has a few that will delight any garden enthusiast.
One such spot is the Chester Community Garden, which features a variety of flowers, vegetables, and herbs tended by local gardeners.
It’s a serene place to walk around or sit and enjoy the tranquility.
If you visit during the summer, you might catch some community events like gardening workshops or local farmers’ markets.
These hidden gems add to the charm of Chester and are perfect for a quiet afternoon.
Maintaining Health and Wellness
For those who like to keep up with their fitness, Chester offers several options for health and wellness.
The Chester Fitness Center provides a range of equipment and classes, from yoga to high-intensity interval training (HIIT).
Staying active during your trip will be a breeze with these facilities.
Additionally, you might enjoy some holistic health options, such as massage therapy and acupuncture.
To explore similar wellness activities, consider looking intoleading yoga retreats not too far away in Rhode Island.
Stargazing at Chester Observatory
A visit to the Chester Observatory offers a fascinating glimpse into the night sky.
They regularly host stargazing events where you can see planets, stars, and galaxies through their telescopes.
Observatory staff often provide educational talks, making it a fun and informative experience for all ages.
Summers are particularly popular for stargazing as the skies are clear and the nights are warm.
Be sure to bring a jacket, as temperatures can drop after sunset.
Visiting the Chester Historical Society
Another fascinating place for history lovers is the Chester Historical Society.
This local organization offers a wealth of information about the town’s past.
You can explore their museum, which features exhibits on Chester’s colonial history, local industries, and notable figures.
The museum also showcases a variety of artifacts that give you a deeper understanding of the town’s heritage.
Volunteers are often available to provide guided tours and answer any questions you might have.
Be sure to check their website for special events and lectures that might coincide with your visit.
Exploring the Chester Village Market
The Chester Village Market is a great place to experience local culture and buy unique products.
This charming market offers a wide variety of goods, from fresh produce to handmade crafts.
On weekends, you might find farmers selling fresh vegetables, fruits, and dairy products.
Local artisans also display their handmade jewelry, pottery, and other crafts, making it a perfect spot to pick up souvenirs.
Visiting this market provides a great way to support local businesses and take home a piece of Chester.
Tasting Local Flavors at Hilltop Orchards
Hilltop Orchards is another must-visit spot for those who appreciate fresh produce and local flavors.
This family-owned orchard offers apple picking in the fall and sells a variety of homemade goods year-round.
You can enjoy their famous apple cider donuts and fresh apple cider during your visit.
The orchard also produces its own line of wines, which you can sample in their cozy tasting room.
People often recommend visiting during the fall when the orchard is in full swing and the trees are laden with ripe apples.
Exploring Local Art Galleries
Art enthusiasts will find plenty to appreciate in Chester’s local art galleries.
One such gallery is the Rainbow Gallery, which showcases a diverse range of works from local artists.
You’ll find everything from paintings to sculptures, all celebrating the beauty and creativity of the region.
Many pieces are available for purchase, making it a great place to buy unique art for your home.
The gallery often hosts exhibitions and artist talks, providing an opportunity to engage with the creative community.
Attending Local Farmers Markets
Farmers markets are the heartbeat of many New England towns, and Chester is no exception.
The Chester Farmers Market is a vibrant spot where you can buy fresh, local produce and homemade products.
Vendors offer everything from organic vegetables and fruits to artisan breads and cheeses.
The market also features local craftspeople selling handmade goods, making it a perfect place for gift shopping.
Visiting farmers markets is a great way to support local agriculture and get a taste of the community’s flavor.
If you love exploring farmers markets, you might enjoyseeing thriving markets in nearby areas.
Discovering Unique Wildlife
Nature lovers will delight in the opportunity to discover unique wildlife in Chester.
Railroad Hill Wildlife Sanctuary is a hidden gem that offers a sanctuary for various bird species and other wildlife.
This area is perfect for birdwatching, with several viewing platforms and marked trails.
The sanctuary is also home to small mammals and reptiles, providing a glimpse into the region’s biodiversity.
It’s said that the best time to visit is during early mornings or late afternoons when wildlife is most active.
Touring Local Breweries
For those who enjoy craft beer, touring local breweries can be a fun and educational experience.
One highly recommended brewery near Chester is the Westfield River Brewing Company.
This brewery offers a range of craft beers made from locally sourced ingredients.
Visitors often rave about their IPAs and seasonal brews, which you can sample in their tasting room.
The brewery often hosts events and live music, creating a lively atmosphere perfect for a weekend visit.
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Experiencing Local Music and Festivals
Chester’s vibrant cultural scene includes a variety of local music events and festivals.
During the summer months, the town often hosts outdoor concerts and music festivals that attract both locals and visitors.
One popular event is the Chester Music Festival, which features performances from local bands and musicians.
The festival atmosphere is lively, with food vendors and family-friendly activities adding to the fun.
These events provide a great opportunity to immerse yourself in the local culture and enjoy some fantastic music.
Exploring Nearby State Parks
Chester’s location makes it an excellent base for exploring nearby state parks.
Otis State Forest is a short drive away and offers beautiful hiking trails and serene picnic spots.
Birch Hill Wildlife Management Area is another nearby destination perfect for outdoor enthusiasts.
These parks provide opportunities for hiking, fishing, and wildlife observation.
They are less crowded during weekdays, making them ideal for a peaceful day out in nature.
If you enjoy hiking, don’t forget to check out some of the popular trails in Rhode Island for more adventure.
Learning at the Chester Library
The Chester Library is more than just a place to borrow books.
It’s a community hub offering various programs and events for all ages.
You can participate in book clubs, attend lectures, or join children’s storytime sessions.
The library also has a local history section, providing a wealth of information about Chester’s past.
Check their website for the schedule of events and make sure to stop by during your visit.
Relaxing in Local Quaint Cafes
Chester is home to several quaint cafes perfect for relaxing with a cup of coffee or tea.
One lovely spot is Cup O’ Joes, where you can enjoy freshly brewed coffee and delicious pastries.
The cafe has a cozy atmosphere, making it an excellent place to unwind or catch up with friends.
If you prefer tea, head to Tea Cozy Cafe, which offers a variety of teas and light snacks.
The welcoming vibe and friendly staff make these cafes a favorite among locals and visitors alike.
Enjoy a Night at the Star Theatre
No trip to Chester is complete without spending an evening at the Star Theatre.
This historic theatre offers a variety of performances, from classic plays to modern productions.
The intimate setting allows you to get up close to the action, creating a memorable theater experience.
The theatre often hosts special events and guest performances, so be sure to check their schedule in advance.
It’s said that attending a show here is a must-do activity for any visitor to Chester.
Chill on the Chester Green
The Chester Green is a central spot where you can relax and enjoy the town’s atmosphere.
This charming green space often hosts community events like outdoor concerts and farmers markets.
It’s a perfect place for a leisurely picnic or a quiet afternoon reading under the trees.
The Green is also conveniently located near several shops and cafes, making it easy to grab a bite to eat or do some light shopping.
Locals often mention that the Chester Green is the heart of the town, offering a welcoming space for everyone.
Conclusion
With a rich tapestry of activities, historical sites, and local flavors, Chester, Massachusetts, is a hidden gem worth exploring.
Whether you’re a nature enthusiast, history buff, or someone who enjoys discovering local culture, Chester has something for everyone.
Plan your trip carefully to make the most of your visit and enjoy all that this charming town has to offer.
From outdoor adventures to relaxed evenings at local cafes, Chester provides an array of memorable experiences waiting to be discovered.

Avery Ingram
Contributor