Welcome to Chesterfield, Massachusetts
Experience the Rural Beauty of Chesterfield
Nestled in the hills of Hampshire County, Massachusetts, Chesterfield is a charming rural town known for its scenic landscapes, agricultural heritage, and tight-knit community. Nature enthusiasts and photographers will love Chesterfield Gorge, a tranquil natural wonder carved by the East Branch of the Westfield River, complete with hiking trails leading to picturesque viewpoints. The town’s farming roots run deep, with local farms offering farm-to-table freshness and pick-your-own produce that connect visitors to Chesterfield’s agricultural character. History comes alive in the West Chesterfield Historic District, where well-preserved colonial-era homes and landmarks reflect the town’s rich past, while the Chesterfield Library serves as a welcoming hub for reading, learning, and community programs. Throughout the year, seasonal festivals and town meetings bring neighbors together, showcasing the strong community spirit that defines the town. Whether you’re seeking a peaceful retreat, a taste of agricultural heritage, or genuine small-town connection, Chesterfield offers it all — where rural charm meets community warmth.
Visit Local Businesses
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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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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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
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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
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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
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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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Fresh farm grown veggies and fruits, free range eggs, Alchemy Edible artisan chocolates, herbal products and more!
505 Main Road
Chesterfield, MA 1012
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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
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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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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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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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We enjoy and care for more than 100 special places Ð nearly 25,000 acres Ð all around Massachusetts. We are actively building an extended family of friends and neighbors across the state that can help in their different ways. We protect the distinct character of our communities and inspire a commitment to our special places. Our passion is to share with everyone the irreplaceable natural and cultural treasures we care for.
Mailing Address100 Main Street, Suite 1Florence MA 01062
100 Main Street
Ashfield, Chesterfield, Cummington, Windsor, MA 1062.0
United States
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