Things to Do in Cummington Massachusetts
Updated July 5, 2024 at 3:32 pm
Discover the charming attractions and hidden gems of Cummington, Massachusetts, from scenic outdoor adventures to local history and cultural experiences.

Discover the Historic Charm of Cummington
Cummington, Massachusetts, is a quaint, scenic town nestled in the Berkshire Hills.
It’s rich in history and natural beauty, offering a serene escape from the hustle and bustle of city life.
For history enthusiasts, visiting the Cummington Historical Museum is a must.
The museum houses fascinating exhibits that provide insights into the town’s past.
The collections include artifacts from the 19th century and memorabilia from local historical events.
Another significant landmark is the William Cullen Bryant Homestead.
This historic home is named after the famous poet and journalist William Cullen Bryant, who was born in Cummington in 1794.
Visitors can tour the well-preserved home and grounds, gaining a deeper appreciation for Bryant’s life and work.
If you appreciate literature, strolling around the property will evoke a sense of walking in Bryant’s footsteps.
Explore Nature and Outdoor Activities
Cummington’s natural landscape makes it an ideal destination for outdoor enthusiasts.
One of the top spots is the Trustees’ Bryant Homestead.
It offers several miles of hiking trails with breathtaking views of the Westfield River Valley.
The trails range from easy to moderate, catering to various hiking skill levels.
Additionally, Cummington’s location in the Berkshires provides access to an array of nearby hiking and biking trails.
The Cummington Fairgrounds, home to the annual Cummington Fair, transforms into a peaceful spot for a leisurely stroll or picnic during the off-season.
Families especially enjoy the fairgrounds, which offer plenty of open space for kids to play and explore.
If you’re a fan of cycling, you’ll find that Cummington and the surrounding area have some of the best cycling trails in Massachusetts.
The quiet country roads and scenic routes make for an enjoyable ride.
During the winter, the area around Cummington also becomes a playground for snow sports.
Cross-country skiing is particularly popular, with many trails available for exploration.
There’s something magical about gliding through snow-covered landscapes.
Attend Local Events and Festivals
One of Cummington’s highlights is its vibrant community events.
The Cummington Fair, held every August, is a significant yearly event.
This traditional country fair has been running for over 150 years and features livestock exhibits, agricultural shows, and classic fairground attractions.
It’s the perfect opportunity to experience local culture and heritage.
Music lovers will appreciate the Old Creamery Co-op, a community hub that hosts various musical events and open mic nights.
The co-op also has a delightful café that serves locally sourced food, making it a great spot to relax and enjoy some live music.
For art enthusiasts, the Cummington Cultural District offers art showings, workshops, and classes throughout the year.
The district is known for its support of local artists, and attending one of their events is a great way to immerse yourself in the local arts scene.
Savor Local Dining Experiences
While Cummington may be small, it boasts some excellent dining options.
The Old Creamery Co-op stands out as a must-visit.
It’s a member-owned cooperative that sources ingredients from local farms and producers.
The café offers a wide range of delectable dishes, from hearty sandwiches to fresh salads.
The Old Creamery Co-op is celebrated for its baked goods, especially its pastries and bread.
If you have a sweet tooth, their selection of desserts will not disappoint.
For a unique dining experience, visit the Red Bucket Sugar Shack.
This charming spot is famous for its maple syrup produced right on the premises.
They serve delicious pancakes that pair perfectly with their syrup, making it a popular breakfast destination.
If you’re in Cummington during sugaring season (late February to early April), consider taking a tour of the sugar shack to see how maple syrup is made.
It’s a fascinating process and gives you a greater appreciation for this quintessential New England product.
Shop at Local Boutiques and Farmer’s Markets
Cummington offers delightful shopping experiences, particularly if you’re interested in local, handmade goods.
One of the top spots is the Cummington Farmers’ Market.
Held every Saturday from June to October, the market features fresh produce, handmade crafts, and artisanal products from local vendors.
It’s a fantastic place to pick up unique souvenirs and support the local economy.
Additionally, you’ll find small boutiques and gift shops around town that sell a variety of charming items.
From handcrafted jewelry to locally made candles, there’s something for everyone.
These shops often carry products made by local artisans, ensuring that you’re getting something genuinely unique.
Shopping local not only helps support small businesses but also gives you a chance to bring home a piece of Cummington’s charm.
Accommodation Options in Cummington
Finding the perfect place to stay can make your trip to Cummington even more delightful.
While the town itself may not have a wide array of hotels, its surrounding areas do offer a variety of accommodations to fit different tastes and budgets.
A notable place to consider is the Little House on the Farm & Guest Barn.
This charming bed and breakfast is renowned for its cozy atmosphere and warm hospitality.
The guest rooms are tastefully decorated, providing a home-away-from-home feel.
A complimentary breakfast featuring locally sourced ingredients is included, making mornings a true delight.
Its location also provides easy access to many of Cummington’s local attractions.
Visit Local Wineries and Breweries
For those who enjoy local beverages, the nearby Berkshire Brewing Company is a must-visit.
Located a short drive from Cummington, this brewery offers a variety of craft beers that are beloved by locals and visitors alike.
The brewery tour provides insights into the brewing process and allows for some delightful tastings.
Many find the brewery’s setting inviting, often describing it as a hub of community gatherings.
Another great spot is the Black Birch Vineyard, situated around 20 minutes from Cummington.
This vineyard produces a range of wines that capture the essence of the local terroir.
The vineyard’s tasting room offers stunning views of the surrounding landscape, making it a perfect spot for a relaxing afternoon.
Both venues often host special events and tastings, so be sure to check their schedules for any upcoming happenings.
Explore Local Parks and Natural Reserves
Cummington’s parks and natural reserves are ideal for a peaceful retreat into nature.
Petticoat Hill Reservation is one of the area’s hidden gems.
This reserve offers several hiking trails that wind through scenic forests and meadows.
The trails are relatively easy, making them suitable for hikers of all skill levels.
Petticoat Hill is particularly magnificent during the fall when the foliage transforms into a vibrant tapestry of red, orange, and yellow.
Wildlife enthusiasts will also love the varied bird species that can be spotted in the park.
Another great outdoor spot is Deer Hill State Reservation.
This area features more challenging trails and rewards hikers with panoramic views of the Berkshires.
The reservation is less crowded than other parks, offering a tranquil experience for those who prefer solitude.
Engage in Creative Workshops and Classes
If you’re looking to tap into your creative side, Cummington provides several opportunities to do so.
The Cummington Community House often hosts various workshops, ranging from painting and pottery to knitting and woodworking.
These workshops are generally taught by local artisans and provide an excellent way to learn a new skill or hobby.
Attending one of these classes is also a fantastic way to meet locals and immerse yourself in the community.
An added benefit is that many of the items you create can serve as unique souvenirs of your time in Cummington.
For more advanced art enthusiasts, the Snow Farm: The New England Craft Program offers intensive courses in everything from glassblowing to ceramics.
These courses are usually held over several days and provide in-depth instruction and practice in various artistic disciplines.
Sample Local Treats at Bakeries and Cafes
A trip to Cummington would not be complete without indulging in some local treats.
A favorite spot among both locals and visitors is the Bread Euphoria Bakery.
Known for its artisanal bread and pastries, this bakery uses high-quality, locally sourced ingredients.
Their croissants and sourdough bread often have people coming back for more.
In addition to baked goods, Bread Euphoria also serves delectable meals, making it a perfect spot for brunch.
The rustic, welcoming atmosphere adds to why many find this place so charming.
If you’re looking for a more laid-back café vibe, Elmer’s Store in neighboring Ashfield is worth the short drive.
This community hub offers delicious food, strong coffee, and a welcoming environment that makes you feel right at home.
Seasonal Attractions and When to Visit
Cummington’s charms vary with the seasons, each offering unique experiences and attractions.
Spring and summer are ideal for exploring outdoor trails and visiting local farms and farmer’s markets.
The temperate weather makes it perfect for hiking, picnicking, and other outdoor activities.
Fall, with its spectacular foliage, is another excellent time to visit.
The area transforms into a colorful paradise, providing breathtaking views and fantastic photo opportunities.
The Cummington Fair held in late summer is a must-see event, offering a mix of local culture, history, and fun activities.
Winter brings its own kind of magic to Cummington.
Snow covers the landscapes, transforming the town and its surroundings into a winter wonderland.
This season is perfect for activities like cross-country skiing and snowshoeing.
If you’re planning a winter visit, make sure to check out the local weather forecasts and trail conditions ahead of your trip.
Educational Opportunities and Learning Experiences
For those keen on continuing their education or learning something new, Cummington offers some intriguing educational opportunities.
The William Cullen Bryant Homestead, besides being a historical landmark, often hosts educational programs and workshops that delve deeper into the life and works of the poet.
These programs are particularly enriching for literature enthusiasts and offer a unique perspective on 19th-century American writing.
Similarly, the Cummington Historical Museum isn’t just about exhibits; it frequently organizes lectures and interactive sessions about the town’s history.
These events provide visitors with a deeper understanding of local heritage and culture.
Engaging in these learning experiences can be a rewarding way to connect more deeply with the community and its history.
For family-friendly educational outings, the Old Creamery Co-op hosts occasional workshops related to food, farming, and sustainability.
These sessions are not only educational but also fun, making them perfect for both adults and children.
Whether it’s a cooking class or a farm tour, these activities add a hands-on element to your visit.
Family-Friendly Activities
If you’re traveling with family, Cummington has plenty of options to keep everyone entertained.
The Cummington Fair is an obvious highlight, offering activities that delight children and adults alike.
From petting zoos and pony rides to amusement rides and games, there’s something for everyone at this annual event.
During the fair, it’s common to find local vendors selling handmade crafts, which can make lovely souvenirs.
For a more laid-back family outing, visit the Cummington Fairgrounds during the off-season.
With plenty of open space, it’s a great spot for picnics and family games.
Kids can run around freely, making it a relaxing day for parents as well.
If your family enjoys nature, the hiking trails around the William Cullen Bryant Homestead are perfect.
The trails are easy enough for kids but still offer beautiful scenery that everyone will appreciate.
Unique Experiences and Hidden Gems
While Cummington may be small, it’s full of unique experiences that can make your visit unforgettable.
One hidden gem is the Bryant Free Library, a charming little library that often flies under the radar of many visitors.
Established in 1872, this quaint library is a wonderful place to relax and maybe catch up on some reading.
The library often hosts small community events, making it a local favorite.
Another delightful find is the annual Cummington Open Studio Tour, where local artists open their studios to the public.
Held every fall, this event allows you to see where and how artists work and perhaps purchase some unique art pieces directly from the creators.
For a more adventurous hidden gem, try exploring the Westfield River.
The river offers excellent opportunities for fishing, kayaking, and even just relaxing by the water.
It’s especially serene in the early morning or late afternoon when the sunlight shimmers on the water.
Plan Your Trip to Cummington
Planning your trip to Cummington involves more than just choosing the dates; it’s about making the most of what this charming town has to offer.
Start by deciding what season you want to visit in.
Each season comes with its unique set of attractions, as Cummington transforms with the changing weather.
If you’re planning to visit during a festival or event like the Cummington Fair, make sure to book your accommodation well in advance.
Local inns and bed-and-breakfasts tend to fill up quickly during these peak times.
Map out the local attractions and decide which ones are ‘must-visits’ for you.
This way, you can prioritize and make the most of your time.
It’s also a good idea to check if any local businesses or attractions offer discounts or promotions.
Keeping an eye on community boards or the town’s website can help you find great deals.
Don’t forget to pack according to the season.
Layered clothing is advisable during spring and fall, while winter needs more robust snow gear for outdoor activities.
Lastly, make sure to have a flexible itinerary.
Sometimes, the best experiences come from unexpected detours and spontaneous decisions.
Shopping Recommendations and Local Markets
Shopping in Cummington provides an excellent opportunity to support local artisans and explore unique products.
The Cummington Farmers’ Market is perhaps the best place to do this.
Held every Saturday from June to October, the market offers fresh produce, handmade crafts, and specialty items that you won’t find anywhere else.
One favorite among locals is the assortment of homemade jams and jellies, which make great gifts or personal treats.
For those interested in handmade jewelry, several artisans sell beautiful, unique pieces.
These often incorporate local materials and reflect the natural beauty of the Berkshires.
Small boutiques around town also provide a lovely shopping experience.
One recommended spot is Many Hands Fiber Arts, a boutique dedicated to locally made yarn and fiber arts supplies.
If you’re into knitting or crochet, this shop is a must-visit.
You can find just the right yarn for your next project and maybe even get some tips from the knowledgeable staff.
Shopping in Cummington is not just about buying; it’s about experiencing the local culture and supporting the community.
Relaxing Spa and Wellness Options
Looking to unwind and relax during your stay? Cummington offers a few delightful spa and wellness options to consider.
The Kushi Institute, located a short drive away, is a renowned center for macrobiotic education and healing.
They offer various wellness programs and spa treatments geared towards holistic health.
Another recommended wellness destination is the Integrative Massage and Bodywork Studio, where you can book a variety of massage treatments.
Whether you’re looking for deep tissue, Swedish, or hot stone massage, this studio has it all.
The experienced therapists take a personalized approach to ensure you get the most benefit from your session.
Wellness isn’t just about treatments; it’s also about staying active and enjoying the outdoors.
Practicing yoga at one of many scenic spots around Cummington can be incredibly rejuvenating.
Imagine doing your sun salutations surrounded by the picturesque beauty of the Berkshires.
Tips for an Enjoyable Visit
To make your stay in Cummington as enjoyable as possible, here are some handy tips.
First, always check the local weather forecast before heading out.
Cummington’s weather can be quite variable, especially during transitional seasons like spring and fall.
Second, make reservations for popular dining spots and accommodations well in advance, especially if you’re visiting during peak seasons or local events.
Third, if you’re an outdoor enthusiast, familiarize yourself with the local trails and parks.
Many trails are well-marked, but having a map or using a trail app can save you from any potential confusion.
Fourth, engage with the local community.
Don’t hesitate to ask locals for recommendations.
They often have the best advice on hidden gems and must-see attractions.
Finally, consider purchasing a few souvenirs from local shops.
It’s a great way to remember your trip and support the community.
Wrap-Up and Final Considerations
Visiting Cummington, Massachusetts, promises a blend of history, nature, and local charm.
Whether you’re exploring the William Cullen Bryant Homestead or strolling through the Cummington Farmers’ Market, there’s something for everyone.
Take the time to immerse yourself in the community and culture, and you’ll leave with unforgettable memories.

Avery Ingram
Contributor