Welcome to Chester, Massachusetts
Discover the Tranquil Charm of Chester
Welcome to Chester, a picturesque town nestled in the foothills of the Berkshires in Western Massachusetts. Known for its peaceful ambiance, natural beauty, and tight-knit community, Chester is an ideal destination for those seeking a tranquil escape.
Nature’s Oasis
Keystone Arches
Marvel at the Keystone Arches, an engineering marvel and historic railroad bridge that spans the Westfield River. Take a scenic hike along the trail and appreciate the craftsmanship of these magnificent stone arches, transporting you back in time.
Chester-Blandford State Forest
Explore the vast Chester-Blandford State Forest, offering hiking trails, fishing spots, and serene picnic areas. Embrace the tranquility of nature as you wander through the lush forests and discover the hidden gems of this beautiful state forest.
Charming Historic Sites
Chester Railway Station
Visit the Chester Railway Station, a well-preserved historic site that reflects the town’s connection to the railroad industry. Learn about Chester’s history and enjoy the nostalgic atmosphere surrounding this charming station.
Chester Center Historic District
Stroll through the Chester Center Historic District, where colonial-era homes and quaint architecture showcase the town’s rich heritage. Explore local shops and eateries that contribute to the small-town charm of Chester.
Community Spirit
Chester Theatre Company
Engage with the vibrant arts community at the Chester Theatre Company, offering thought-provoking performances in an intimate setting. Experience the talent and creativity that thrive within Chester’s artistic circles.
Local Events
Chester hosts various community events throughout the year, fostering a strong sense of community. From seasonal festivals to farmers’ markets, these gatherings provide opportunities to connect with neighbors and celebrate the unique spirit of Chester.
Outdoor Recreation
Chester-Blandford Ski Area
In the winter, embrace outdoor recreation at the Chester-Blandford Ski Area. Enjoy skiing and snowboarding in a family-friendly environment, surrounded by the scenic beauty of the Berkshire Mountains.
Plan Your Visit
Whether you seek outdoor adventures, historical exploration, or a peaceful retreat, Chester has something for everyone. Immerse yourself in the natural beauty, discover the town’s history, and become part of the welcoming community that defines Chester.
Come and experience Chester – where history meets nature, and community becomes family.
Visit Local Businesses
For lovers of history and railroads, it would be hard to beat the appeal of Chester Station and the Keystone Arches, which share a National Historic Landmark designation bestowed by the National Park Service. The significance inherent in these sites as elements of the Western Railroad, c 1841, include the world’s first mountain railroad; the first railroad built through wilderness, the first railroad built by large numbers of immigrant laborers and the first place in the world where pusher engines were employed. The Keystone Arches are the first cluster of stone arch railroad bridges built in America and the Station is one of only four examples of the timber frame stations built by the Western Railroad that still exist and the most intact. This project was the laboratory for the development of long-distance developmental railroads, which built America. The sections of roadbed between the Arches carry evidence of the hand labor that pushed this line through what remains today the largest roadless wilderness, following the first National Wild & Scenic River and the longest stretch of free-flowing river left in the state of MA. This overload of natural wonder is wonderfully enhanced by the dry laid, hand-chiseled marvels that carry the rails up to 70 ft. above the water. The hike along the Keystone Arch Bridges Trail is stunningly enhanced by a visit to the Station Museum, which houses artifacts explaining the incredible struggle that triumphed over the elements to reveal the full potential of the fledgling railroad technology.
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10 Prospect St.
Chester, MA 1011.0
United States
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Davenport Child Care was founded in 1997 at the old Davenport School in Chesterfield, Massachusetts by Therese Doyle Brigley. The tenth in a family of fifteen children, Therese has helped care for children her whole life, including as an at-home childcare provider and a preschool teacher. Today, Davenport’s home is in the lower level of the Hilltown Community Development Corporation (CDC) building. Six teachers, Therese and one staff member serve over 30 families through infant, toddler and pre-school programs.
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387 Main Rd
Chesterfield, MA 1012.0
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Hilltown Tree and Garden is seen as the premier horticulture firm in Western Massachusetts. They employ Massachusetts Certified Horticulturists, Massachusetts Certified Arborists, and Massachusetts Licensed Pesticide Applicators. The team has almost 100 years of professional horticultural and arboriculture experience.
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Pynchon Rd
Chesterfield, MA 1012
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Infants through advanced riders. Problems, restarts, mounted and unmounted, horse therapy. Horses connect and communicate through body language, energy and space. Body riding is safer, more harmonious and healthier for horses. Also donkey/pony rides and children's lessons. Licensed, will travel. (413) 354-7744
Chester, MA 1011
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Hilltown Sled Dogs, an Alaskan Husky Team in Western Mass offers fall rig rides, dog yard tours, hikes with a husky & lessons with our dogs or yours!
Chesterfield, MA 1012
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Mailing AddressP.O. Box 19Chester MA 01011-0019
613 Route 20
Chester, MA 1011
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As a Cuddlist, I provide nurturing therapeutic touch and companionship. As a Consent Educator, I offer individual coaching and group workshops on communication and consent.Mailing AddressPO Box 24West Chesterfield 01084
Chesterfield MA 01012
Chesterfield, MA 1012
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Accounting, bookkeeping, tax preparation. Established 1990.Mailing Address31 Stage RoadWilliamsburg MA 01096
31 Stage Road
Chesterfield, MA 1012
United States
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Five element spirit-based practice, using acupuncture and essential oils to help restore balance and support wellness. Specializing in improved sleep and energy, womenÕs issues, and emotional health. Offices in Chesterfield and Northampton. LGBTQ - Deaf friendly. When the body and mind are aligned, the spirit can soar!Mailing AddressPO Box 47Chesterfield MA 01012
72 Center St
Chesterfield, MA 1060.0
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Mentoring, Spiritual counseling, Personal and Professional Development, Spiritual Walkabouts, Business Consulting. Learn to live a more joyful, creative and authentic life despite the chaos and crises surrounding us. Sliding scale available.Mailing AddressPO Box 264Chesterfield 01012
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PO Box 264
Chesterfield, MA 1012
United States
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Water well drilling, water pump sales and service, water treatment.Mailing AddressP.O. Box 117West Chesterfield MA 01084
130 Cummington Road West
Chesterfield, MA 1012
United States
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Quiet earth-shelter off-grid home with two guest rooms, Overnight retreat accommodations on 12 acres with woodland trails. Open May through October.Mailing Address261 South StreetChesterfield MA 01012
261 South Street
Chesterfield, MA 1012
United States
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Hilltown Easy Ride is a van service for seniors over 60 and veterans in the towns of Chesterfield, Cummington, Goshen, Plainfield and Worthington. The primary goal of the service is to provide transportation in a rural area with no other public transportation options. In addition to regularly scheduled shopping trips to Pittsfield and Northampton, riders may also get to medical appointments and attend social trips through the local Councils on Aging (COAs).
Interested riders must be pre-approved for eligibility with this FRTA form. You can print and send directly to FRTA, or our Transportation Coordinator will be happy to help you.
Our dispatcher Ed Pelletier is part-time but checks messages daily. Please leave a detailed message with your name, date, time and destination and we will check the schedule and get back to you quickly. You can also email ride@hilltowncdc.org
Hilltown Easy Ride is a Demand Response service of the Franklin Regional Transit Authority (FRTA). For service, riders must call or email our dispatcher at least 48 hours in advance. The dispatcher will then let you know if the van and driver are available at that time. It is not a taxi service and trips are sometimes shared with others as schedules permit.
$1.25 - one way trip within the same town
$1.75 - one way trip to an adjacent towns
$2.25 - one way trip beyond adjacent towns
All trips to Senior Centers are half fare.
Fares are paid in cash and driver is unable to make change. Punch cards in $5 and $10 increments are available to conveniently prepay for multiple trips. For questions please call (413) 296 - 4232
We are pleased to be able to offer the use of the Easy Ride Van to area Councils on Aging for Group Outings. Cost is based on the number of hours for the trip and an 8 person minimum is required.
$3 per person for a three hour trip
$4 per person for a four hour trip
$5 per person for a five hour trip
These low rates are made possible through a grant from Highland Valley Elder Services.
Hilltown CDC also has grant funding to supplement the van for occasional medical rides for appointments outside of the van service area, or when there is a scheduling conflict with the van. The Hilltown Driver Pool is a group of approved drivers in the community who can take riders in their personal vehicles to fill this occasional need. Hilltown CDC coordinates these rides and reimburses the driver. All rides must be booked through dispatch and the number of rides are limited by grant funding availability.
Hilltown CDC operates its programs, services, and activities in compliance with federal and state nondiscrimination laws including Title VI of the Civil Rights Act of 1964, the Civil Rights Restoration Act of 1987, related statutes and regulations and the Massachusetts Public Accommodation Law, M.G.L. c272 92a, 98, 98a. For more information, click here.
387 Main Road
Chesterfield, MA 1012.0
United States
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Thinking of starting a new business in the Hilltowns? We can help. We offer business consulting for both new or existing Hilltown businesses. We offer both one-on-one assistance, and free classes tailored for the needs of small business owners. Call today. We can guide you every step of the way.Mailing AddressP.O. Box 17Chesterfield MA 01012
387 Main Road
Chesterfield, MA 1012
United States
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PYO apples and blueberries seasonally. Maple syrup and eggs available year round. Hay and cordwood orders taken year round. Call for availability. 413-667-3640
410 Skyline Trail
Chester, MA 1011
United States
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Fresh farm grown veggies and fruits, free range eggs, Alchemy Edible artisan chocolates, herbal products and more!
505 Main Road
Chesterfield, MA 1012
United States
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Drowsy Dragon Kitchen is a commercial kitchen on Main Street in Chester. Available for rent. Reasonable rates. We sell our farm's microgreens and low-sugar blueberry jam, syrup and topping/pie filling on Saturdays from 9 am to 2 pm in the historic Pease Store next door.
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15 Main St
Chester, MA 1011
United States
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Year round Farm-stand offering our own free-range eggs and grass-fed/finished beef and lamb. We also produce vegetables, garden starts and woolen yarn.Mailing AddressP.O. Box 263Chesterfield MA 01012
100 Bryant Street
Chesterfield, MA 1012
United States
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Bridging the Digital DivideComputer First AidMy services encompass a wide range of solutions, from diagnosing and fixing technical glitches to offering expert advice on optimizing your digital experience.
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322 East River Road
Chester, MA 1050
United States
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Established 1987. Pizza, grinders, salads, appetizers, specials, take-out, Full bar. Open seven days. Darts, Jukebox. Find us on Facebook.Mailing AddressP.O. Box 86Chester MA 01011
29 Main Street
Chester, MA 1011.0
United States
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Traditional Wood Fired Brick Oven Cooking & Local Market at Old BabeÕs Garage. Featuring Brick Oven Pizza, Breads, Pastries, Soups, Salads, Sandwiches, Roasted & Smoked Meats, Fish & Vegetables. Breakfast, Lunch and Early Dinner Menu Items. 25 years Cooking & Catering Experience. Intimate Event Space Available, Beer & Wine, Spirits & Groceries. Chef Owned & OperatedMailing Address432 Main RoadChesterfield MA 01012
432 Main Road
Chesterfield, MA 1012.0
United States
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Farm-fresh takes on comfort food classics. Meat and veggies from local farms, large selection of craft beers and cocktails with live music weekends.Mailing Address30 Main StChester MA 01011
30 Main St
Chester, MA 1011
United States
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Boarding and grooming for dogs and cats. Indoor/outdoor individual heated quarters. Pet sitting in your home for Chester, Huntington area.Mailing Address280 Bromley RoadHuntington MA 01050
280 Bromley Road
Chester, MA 1011
United States
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Classic yet creative diner fare and homemade baked goodies in a historic setting. Open 7AM-2PM.
241 US-20
Chester, MA 1011
United States
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School-age care program for ages 5-12 years. Before and after school, half-days, school vacations. Summer program. OCCS licensed.Mailing AddressP.O. Box 300Chesterfield MA 01012
30 Smith Road
Chesterfield, MA 1012
United States
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