Winter holiday events in Lenox, MA

Milford 4th Annual Holiday Craft Fair
Sat, Dec 12, 10:00 AM
Milford · VFW Post 4368
Milford 4th Annual Holiday Craft Fair
Sat, Dec 12, 10:00 AM
Milford · VFW Post 4368
Just added
Marching in Purpose
Sun, Mar 8, 2:00 PM
Chester · A Theme Come True
Just added
Marching in Purpose
Sun, Mar 8, 2:00 PM
Chester · A Theme Come True
Going fast
Bach, Brahms, Bolling & Budway — An All Bees Program
Fri, Mar 27, 4:30 PM
Valley Cottage · Valley Cottage Library
Going fast
Bach, Brahms, Bolling & Budway — An All Bees Program
Fri, Mar 27, 4:30 PM
Valley Cottage · Valley Cottage Library
Ghostly Gala: A Mystical Masquerade Social at Wilson Castle
Sat, Oct 10, 6:00 PM
Proctor · Wilson Castle
Ghostly Gala: A Mystical Masquerade Social at Wilson Castle
Sat, Oct 10, 6:00 PM
Proctor · Wilson Castle
Spring Bloom Soap-Making Workshop at Dirigible Brewing – Littleton, MA
Wed, Mar 11, 6:00 PM
Littleton · Dirigible Brewing Company
Spring Bloom Soap-Making Workshop at Dirigible Brewing – Littleton, MA
Wed, Mar 11, 6:00 PM
Littleton · Dirigible Brewing Company
Live Music on the Maple Hill
Sat, Apr 25, 6:00 PM
Goshen · 50 Maple Ave
Live Music on the Maple Hill
Sat, Apr 25, 6:00 PM
Goshen · 50 Maple Ave
FUN EASTER PHOTOS
Sun, Apr 5, 12:00 PM
Middletown · 88 Dunning Rd
FUN EASTER PHOTOS
Sun, Apr 5, 12:00 PM
Middletown · 88 Dunning Rd
Sales end soon
February walk along the Sudbury Reservoir Trail
Saturday at 1:00 PM
Marlborough · Sherman Street
Sales end soon
February walk along the Sudbury Reservoir Trail
Saturday at 1:00 PM
Marlborough · Sherman Street
Stamford St. Patrick's Day Weekend Bar Crawl 2026
Sat, Mar 14, 1:00 PM
Stamford · Hudson Social CT
Stamford St. Patrick's Day Weekend Bar Crawl 2026
Sat, Mar 14, 1:00 PM
Stamford · Hudson Social CT
Just added
Spring Beer Dinner
Tue, Mar 31, 6:00 PM
Westborough · 66 Otis St
Just added
Spring Beer Dinner
Tue, Mar 31, 6:00 PM
Westborough · 66 Otis St
Easter Egg Hunt
Sun, Mar 29, 11:30 AM
Stamford · 1155 Newfield Ave
Easter Egg Hunt
Sun, Mar 29, 11:30 AM
Stamford · 1155 Newfield Ave
Just added
Green Teen Club Spring 2 Session (11yr - 14yr)
Westport · Wakeman Town Farm
Just added
Green Teen Club Spring 2 Session (11yr - 14yr)
Westport · Wakeman Town Farm
Sales end soon
A Grown-Up & Me Traditional Maamoul Cookie Making Experience
Saturday at 12:00 PM
Blackstone · 65 Milk St
Sales end soon
A Grown-Up & Me Traditional Maamoul Cookie Making Experience
Saturday at 12:00 PM
Blackstone · 65 Milk St
Stamford Official St. Patrick's Day Bar Crawl
Tue, Mar 17, 5:00 PM
Stamford · Hudson Social CT
Stamford Official St. Patrick's Day Bar Crawl
Tue, Mar 17, 5:00 PM
Stamford · Hudson Social CT
Stamford's Best St. Patrick's Day Weekend Bar Crawl
Stamford · Best Bars in Stamford
Stamford's Best St. Patrick's Day Weekend Bar Crawl
Stamford · Best Bars in Stamford
Easter Vibes Soap-Making Workshop at Craft Roots Brewing – Milford, MA
Sun, Mar 29, 2:00 PM
Milford · CraftRoots Brewing
Easter Vibes Soap-Making Workshop at Craft Roots Brewing – Milford, MA
Sun, Mar 29, 2:00 PM
Milford · CraftRoots Brewing
O'Halloran Group Ski Day
Fri, Mar 20, 9:00 AM
Newbury · Mount Sunapee Resort
O'Halloran Group Ski Day
Fri, Mar 20, 9:00 AM
Newbury · Mount Sunapee Resort
FERS/CSRS Benefits Workshop - Milford - 03/15/26
Sun, Mar 15, 5:00 PM
Milford · Hilton Garden Inn Milford
FERS/CSRS Benefits Workshop - Milford - 03/15/26
Sun, Mar 15, 5:00 PM
Milford · Hilton Garden Inn Milford
Harbor Point Shamrock Stroll
Sun, Mar 15, 8:00 AM
Stamford · 18 Hbr Pt Rd
Harbor Point Shamrock Stroll
Sun, Mar 15, 8:00 AM
Stamford · 18 Hbr Pt Rd
Feeding Nook: Community Support Group
Tue, Mar 24, 1:00 PM + 5 more
Mount Kisco · Northern Westchester Hospital
Feeding Nook: Community Support Group
Tue, Mar 24, 1:00 PM + 5 more
Mount Kisco · Northern Westchester Hospital

Trends in Lenox

Explore more trends

Milford 4th Annual Holiday Craft Fair

Milford 4th Annual Holiday Craft Fair

Marching in Purpose

Marching in Purpose

Bach, Brahms, Bolling & Budway — An All Bees Program

Bach, Brahms, Bolling & Budway — An All Bees Program

Ghostly Gala: A Mystical Masquerade Social at Wilson Castle

Ghostly Gala: A Mystical Masquerade Social at Wilson Castle

Spring Bloom Soap-Making Workshop at Dirigible Brewing – Littleton, MA

Spring Bloom Soap-Making Workshop at Dirigible Brewing – Littleton, MA

Live Music on the Maple Hill

Live Music on the Maple Hill

FUN EASTER PHOTOS

FUN EASTER PHOTOS

February walk along the Sudbury Reservoir Trail

February walk along the Sudbury Reservoir Trail

Stamford St. Patrick's Day Weekend Bar Crawl 2026

Stamford St. Patrick's Day Weekend Bar Crawl 2026

Spring Beer Dinner

Spring Beer Dinner

Easter Egg Hunt

Easter Egg Hunt

Green Teen Club Spring 2 Session (11yr - 14yr)

Green Teen Club Spring 2 Session (11yr - 14yr)

A Grown-Up & Me Traditional Maamoul Cookie Making Experience

A Grown-Up & Me Traditional Maamoul Cookie Making Experience

Stamford Official St. Patrick's Day Bar Crawl

Stamford Official St. Patrick's Day Bar Crawl

Stamford's Best St. Patrick's Day Weekend Bar Crawl

Stamford's Best St. Patrick's Day Weekend Bar Crawl

Easter Vibes Soap-Making Workshop at Craft Roots Brewing – Milford, MA

Easter Vibes Soap-Making Workshop at Craft Roots Brewing – Milford, MA

O'Halloran Group Ski Day

O'Halloran Group Ski Day

FERS/CSRS Benefits Workshop - Milford - 03/15/26

FERS/CSRS Benefits Workshop - Milford - 03/15/26

Harbor Point Shamrock Stroll

Harbor Point Shamrock Stroll

Feeding Nook: Community Support Group

Feeding Nook: Community Support Group

Things to do around Lenox

Trends in Lenox

1. Valentines day events

2. Comedy show

3. Swing dance

4. Nature

5. Valentines

6. September

7. Hudsonvalley

8. Events happening today near me

9. Dating

10. Winter holiday

11. Valentine

12. Tasting