Holiday markets and local events are more than just opportunities to shop—they’re essential for supporting the smallest businesses in our communities.
From farmers and crafters to shop owners and artisans, these markets provide a lifeline for local entrepreneurs who often pour their passion into every product. Each purchase helps sustain a dream, foster creativity, and strengthen the local economy.
And what better way to support these businesses than during the most magical time of year? Across Western Massachusetts, towns and villages literally transform into enchanting winter wonderland.
Streets are adorned with festive decorations, holiday lights, and cheerful displays, while homeowners add their own glowing touches to neighborhoods. These sparkling settings create the perfect backdrop for holiday markets, where the warmth of community and the spirit of the season come alive.
We’ve put together a list to help you find charming events and markets throughout the region, and make your holiday shopping a meaningful celebration of local talent, creativity, and enterprise.
Amherst
Amherst Winter Farmers Market
🌽 🥐 🧶 ☕️
Dates: Saturdays, November 2024 – April 2025
Details: An indoor market offering fresh local produce, baked goods, and handcrafted items.
Where: Bangs Community Center, 70 Boltwood Walk, Amherst, MA
More Information: Amherst Indy
Who You Support by Taking Part: Local farmers and artisans, promoting sustainable agriculture and the local economy.
Lighting of the Merry Maple
💡 🌭 ☕️ 🎸
Date: December 6, 2024, from 3:00 PM to 6:00 PM
Details: A festive community event featuring the illumination of the Merry Maple tree, accompanied by performances from local groups and family-friendly activities.
Where: North Common, Downtown Amherst, MA
More Information: Amherst Area Chamber of Commerce
Who You Support by Taking Part: Amherst Area Chamber of Commerce and the Amherst Business Improvement District, local businesses and fostering community engagement. Events like this also give a boost to restaurants, boutiques, and coffee shops.
Chicopee
Chicopee Holiday Craft and Vendor Fair
🧶 🌭 ☕️ 🛍️
Date: November 30, 2024
Details: Features diverse crafters and vendors providing holiday shopping opportunities.
Where: Chicopee Comprehensive High School, 617 Montgomery Street, Chicopee, MA
More Information: Chicopee Holiday Craft and Vendor Fair
Who You Support by Taking Part: Local vendors, small businesses, and nonprofit initiatives in the community.
Easthampton
Cottage Street Open Studios & Holiday Sale
🎨 🧶
Dates: December 7–8, 2024
Details: Artists and artisans at One Cottage Street open their studios to the public, offering unique, handcrafted items.
Where: One Cottage Street, Easthampton, MA
More Information: Cottage Street Open Studios & Holiday Sale
Who You Support by Taking Part: Local artists and the creative economy, encouraging the purchase of locally made art and crafts.
Great Barrington
Berkshire Grown Holiday Farmers Market
🌽 🧶 🥩 🧀
Dates: November 20 & December 18, 2024
Details: Features locally grown and produced gifts and foods, including fruits, vegetables, cheeses, and meats.
Where: Housatonic Community Center, 1064 Main Street, Housatonic, MA
More Information: Berkshire Grown Holiday Farmers Market
Who You Support by Taking Part: Regional farmers and food producers, sustaining local agriculture and food systems.
Lenox
NightWood at The Mount
💡 🌭 ☕️ 🎸
Dates: November 15, 2024 – January 6, 2025 (select evenings)
Details: A one-of-a-kind winter event, NightWood transforms the grounds of The Mount into a fantastical blend of light, sound, and design, creating an enchanting outdoor experience. Guests can enjoy artful illuminations, music, and storytelling as they explore the historic site after dark.
Where: The Mount, 2 Plunkett Street, Lenox, MA
More Information: NightWood at The Mount
Who You Support by Taking Part: Cultural heritage preservation and local tourism, as well as the ongoing maintenance and programming of this historic site. Local restaurants also benefit from events like this.
North Adams
FESTIVE Holiday Market at Greylock WORKS
🧶 🌭 ☕️
Date: November 23, 2024
Details: An immersive market celebrating handcrafted goods from the Berkshires and beyond, set in a renovated former mill
Where: Greylock WORKS, 508 State Road, North Adams, MA
More Information: FESTIVE Holiday Market
Who You Support by Taking Part: Regional artisans and the revitalization of historic spaces, fostering economic development.
Northampton
Thornes Marketplace Bag Day
🛍️ 🧆 ☕️ 🥐
Date: November 23, 2024
Details: Participating Thornes merchants offer exclusive discounts, encouraging community shopping.
Where: Thornes Marketplace, 150 Main Street, Northampton, MA
More Information: Thornes Marketplace Bag Day
Who You Support by Taking Part: Local retailers and small businesses, enhancing the local economy.
Grow Food Northampton Winter Market
🌽 🥐 🧶
Dates: Saturdays, November 23, 2024 – April 5, 2025
Details: Held at the Northampton Senior Center, this market offers fresh local produce, baked goods, and handcrafted items.
Where: Northampton Senior Center, 67 Conz Street, Northampton, MA
More Information: Grow Food Northampton Winter Market
Who You Support by Taking Part: Local farmers and artisans, supporting sustainable
Northampton Winter Craft Fair
🧶 📚 ☕️ 🥐 🍕 🎸
Dates: December 7–8, 2024
Details: The 39th annual Northampton Winter Craft Fair benefits CHD’s Big Brothers Big Sisters of Hampshire County. Featuring 90 juried artisans, a children’s book sale, a silent auction (Saturday), live music performances, and delicious food from Hillside Pizza and Catering, this event is a must-visit for holiday shopping. This event is made possible through support from Applied Mortgage, Salon Herdis, Lia Cars, and Daily Hampshire Gazette.
Where: Northampton High School, 380 Elm Street, Northampton, MA
Times: Saturday, 9:30 AM – 4:30 PM; Sunday, 10:00 AM – 4:00 PM
Admission: $5 for adults, free for children; free parking on premises
More Information: CHD Big Brothers Big Sisters Facebook Event Page
Who You Support by Taking Part: Proceeds benefit CHD’s Big Brothers Big Sisters of Hampshire County, supporting one-to-one mentoring relationships for youth. Additionally, the event supports local artisans, musicians, and small businesses.
Pittsfield
Downtown Festive Frolic
💡 🎸 ☕️ 🛍️ 🧆
Dates: December 6–7, 2024
Details: A weekend of holiday activities, including tree lighting, caroling, and local shops offering special promotions.
Where: Downtown Pittsfield, MA
More Information: Downtown Festive Frolic
Who You Support by Taking Part: Downtown businesses and community engagement, fostering a vibrant local economy.
Shelburne Falls
Moonlight Magic
💡 🎸 ☕️ 🛍️ 🧆
Date: November 29, 2024
Details: A festive evening of holiday shopping, music, and lights in the historic village of Shelburne Falls.
Where: Bridge Street and Main Street, Shelburne Falls, MA
More Information: Moonlight Magic
Who You Support by Taking Part: Local shops, artisans, and performers, preserving the unique character of Shelburne Falls.
Springfield
Bright Nights at Forest Park
💡
Dates: November 27, 2024 – January 1, 2025
Details: An annual holiday lights display featuring over 675,000 lights along a three-mile drive through Forest Park.
Where: Forest Park, 300 Sumner Avenue, Springfield, MA
More Information: Bright Nights at Forest Park
Who You Support by Taking Part: Local tourism and community traditions, benefiting the city’s cultural events.
Stockbridge
Stockbridge Main Street at Christmas
💡 🎸 ☕️ 🛍️ 🧆 🚘
Dates: December 6–8, 2024
Details: The town reenacts Norman Rockwell’s famous painting, featuring vintage automobiles, holiday activities, and festive decorations.
Where: Main Street, Stockbridge, MA
More Information: Stockbridge Main Street at Christmas
Who You Support by Taking Part: Local businesses, the Stockbridge Chamber of Commerce, and efforts to preserve the cultural heritage of the Berkshires.
West Springfield
The Old Deerfield Holiday Sampler Craft Fair
🧶 💍 ☕️ 🥐 🧆 🌭 🎸
Details: A cherished annual event that brings together over 200 juried crafters, designers, and artists, offering a diverse array of handcrafted items such as mixed media, ceramics, jewelry, specialty foods, and fine art. Attendees can explore a miniature New England village circa 1897, participate in free family craft activities, and visit with Santa. The event also features live music and encourages visitors to vote for the most festively decorated booth. Proceeds benefit the Pocumtuck Valley Memorial Association, a non-profit dedicated to preserving local crafts and history.
Dates: November 16–17, 2024
Times: Saturday 9:00 AM – 5:00 PM; Sunday 10:00 AM – 4:00 PM
Location: Eastern States Exposition’s Better Living Center, Gate 9, 875 Memorial Ave., West Springfield, MA 01089
Admission: $8 for adults; children 12 and under free
More Information: Old Deerfield Holiday Sampler
Who You Support by Taking Part: By attending, you support local artisans and contribute to the preservation of the region’s cultural heritage.
Williamstown
Holiday Walk Weekend
🧶 🎁 🧆 ☕️ 🥐 🎸
Dates: December 7–8, 2024
Details: Features a Reindog Parade, artisan markets, and holiday decorations throughout the town.
Where: Spring Street, Williamstown, MA
More Information: Holiday Walk Weekend
Who You Support by Taking Part: Local businesses, regional artisans, and community-focused initiatives, promoting a festive and inclusive atmosphere.
