Winter holiday events in Great Barrington, MA

Sales end soon
Institute at UConn
Thursday at 7:00 PM
Storrs · UConn, 441 Susan Herbst Hall (SHH), South Wing, 365 Fairfield Way, Storrs, CT
Sales end soon
Institute at UConn
Thursday at 7:00 PM
Storrs · UConn, 441 Susan Herbst Hall (SHH), South Wing, 365 Fairfield Way, Storrs, CT
Bunny Mosaic
Thu, Mar 19, 5:30 PM
Orange · Stappa Vineyard
Bunny Mosaic
Thu, Mar 19, 5:30 PM
Orange · Stappa Vineyard
New Haven St. Patrick's Day Weekend Bar Crawl 2026
Sat, Mar 14, 1:00 PM
New Haven · Prime 16
New Haven St. Patrick's Day Weekend Bar Crawl 2026
Sat, Mar 14, 1:00 PM
New Haven · Prime 16
Robbie Fulks & FauxMenco
Sat, Mar 21, 7:00 PM
North Haven · Small Batch Cellars
Robbie Fulks & FauxMenco
Sat, Mar 21, 7:00 PM
North Haven · Small Batch Cellars
Going fast
Hole in the Wall (March 8th) + Q&A with playwright, Jeff Hughes
Sun, Mar 8, 3:00 PM
Weston · Lachat Town Farm
Going fast
Hole in the Wall (March 8th) + Q&A with playwright, Jeff Hughes
Sun, Mar 8, 3:00 PM
Weston · Lachat Town Farm
Hole in the Wall (March 6th)
Fri, Mar 6, 7:30 PM
Weston · Lachat Town Farm
Hole in the Wall (March 6th)
Fri, Mar 6, 7:30 PM
Weston · Lachat Town Farm
New Haven Official St. Patrick's Day Bar Crawl
Tue, Mar 17, 5:00 PM
New Haven · Prime 16
New Haven Official St. Patrick's Day Bar Crawl
Tue, Mar 17, 5:00 PM
New Haven · Prime 16
Hole in the Wall (March 22nd) + Q&A with playwright, Jeff Hughes
Sun, Mar 22, 3:00 PM
Weston · Lachat Town Farm
Hole in the Wall (March 22nd) + Q&A with playwright, Jeff Hughes
Sun, Mar 22, 3:00 PM
Weston · Lachat Town Farm
Hole in the Wall (March 15th) + Q&A with playwright, Jeff Hughes
Sun, Mar 15, 3:00 PM
Weston · Lachat Town Farm
Hole in the Wall (March 15th) + Q&A with playwright, Jeff Hughes
Sun, Mar 15, 3:00 PM
Weston · Lachat Town Farm
An Enchanted Evening - North Salem Girls Dance 2026
Friday at 7:00 PM
North Salem · Pequenakonck Elementary School
An Enchanted Evening - North Salem Girls Dance 2026
Friday at 7:00 PM
North Salem · Pequenakonck Elementary School
Going fast
Curious Sprouts Winter Session (Ages 3 - 5 with Caregiver)
Tue, Jan 13, 2:15 PM
Westport · Wakeman Town Farm
Going fast
Curious Sprouts Winter Session (Ages 3 - 5 with Caregiver)
Tue, Jan 13, 2:15 PM
Westport · Wakeman Town Farm
Herbal Medicine 101: Prepare for the Winter Woes
Sun, Oct 11, 10:30 AM
Goshen · All One One All Farm
Herbal Medicine 101: Prepare for the Winter Woes
Sun, Oct 11, 10:30 AM
Goshen · All One One All Farm
Tea Talk and Mental Health
Sat, Mar 28, 12:00 PM + 5 more
New Haven · Dixwell Community House (Q House)
Tea Talk and Mental Health
Sat, Mar 28, 12:00 PM + 5 more
New Haven · Dixwell Community House (Q House)
Just added
Alban Elfed: The Autumn Equinox
Sun, Sep 27, 12:00 PM
Jefferson · The Awen Center
Just added
Alban Elfed: The Autumn Equinox
Sun, Sep 27, 12:00 PM
Jefferson · The Awen Center
Live Music-Dublin Down (FREE/NO TICKET REQUIRED)
Fri, Mar 13, 7:00 PM
East Brookfield · Timberyard Brewing Company
Live Music-Dublin Down (FREE/NO TICKET REQUIRED)
Fri, Mar 13, 7:00 PM
East Brookfield · Timberyard Brewing Company
St Patrick's Day Warm Up
Wed, Mar 4, 5:00 PM + 1 more
Saratoga Springs · Harvey's Restaurant and Bar
St Patrick's Day Warm Up
Wed, Mar 4, 5:00 PM + 1 more
Saratoga Springs · Harvey's Restaurant and Bar
Angry Orchard Adult Egg Hunt
Sat, Apr 4, 12:00 PM
Walden · Angry Orchard Cider House
Angry Orchard Adult Egg Hunt
Sat, Apr 4, 12:00 PM
Walden · Angry Orchard Cider House
Almost full
YES Family Day 2026
Sunday at 9:00 AM
Princeton · Mount Wachusett
Almost full
YES Family Day 2026
Sunday at 9:00 AM
Princeton · Mount Wachusett
Cooking with Nadim in February
Saturday at 11:00 AM
Springfield · North Main Street
Cooking with Nadim in February
Saturday at 11:00 AM
Springfield · North Main Street
Inclusive Maple Sugaring Adventure
Fri, Mar 6, 10:00 AM
Cross River · Trailside Nature Museum
Inclusive Maple Sugaring Adventure
Fri, Mar 6, 10:00 AM
Cross River · Trailside Nature Museum

Trends in Great Barrington

Explore more trends

Institute at UConn

Institute at UConn

Bunny Mosaic

Bunny Mosaic

New Haven St. Patrick's Day Weekend Bar Crawl 2026

New Haven St. Patrick's Day Weekend Bar Crawl 2026

Robbie Fulks & FauxMenco

Robbie Fulks & FauxMenco

Hole in the Wall (March 8th) + Q&A with playwright, Jeff Hughes

Hole in the Wall (March 8th) + Q&A with playwright, Jeff Hughes

Hole in the Wall (March 6th)

Hole in the Wall (March 6th)

New Haven Official St. Patrick's Day Bar Crawl

New Haven Official St. Patrick's Day Bar Crawl

Hole in the Wall (March 22nd) + Q&A with playwright, Jeff Hughes

Hole in the Wall (March 22nd) + Q&A with playwright, Jeff Hughes

Hole in the Wall (March 15th) + Q&A with playwright, Jeff Hughes

Hole in the Wall (March 15th) + Q&A with playwright, Jeff Hughes

An Enchanted Evening - North Salem Girls Dance 2026

An Enchanted Evening - North Salem Girls Dance 2026

Curious Sprouts Winter Session (Ages 3 - 5 with Caregiver)

Curious Sprouts Winter Session (Ages 3 - 5 with Caregiver)

Herbal Medicine 101: Prepare for the Winter Woes

Herbal Medicine 101: Prepare for the Winter Woes

Tea Talk and Mental Health

Tea Talk and Mental Health

Alban Elfed: The Autumn Equinox

Alban Elfed: The Autumn Equinox

Live Music-Dublin Down (FREE/NO TICKET REQUIRED)

Live Music-Dublin Down (FREE/NO TICKET REQUIRED)

St Patrick's Day Warm Up

St Patrick's Day Warm Up

Angry Orchard Adult Egg Hunt

Angry Orchard Adult Egg Hunt

YES Family Day 2026

YES Family Day 2026

Cooking with Nadim in February

Cooking with Nadim in February

Inclusive Maple Sugaring Adventure

Inclusive Maple Sugaring Adventure

Things to do around Great Barrington

Trends in Great Barrington

1. Valentines day

2. Speed dating events

3. Representation

4. Live music

5. Crafts fair

6. Craft fairs

7. Singles

8. Ivan dalia

9. Flea markets

10. Berkshires

11. 420festival

12. Open mic