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Live Events in Littleton, Massachusetts

Littleton, Massachusetts has 8 venues with upcoming events — restaurant, haunted house and venue. 55 events are on the calendar, at spots like Witch's Woods, Collective Premium Cannabis Littleton, The Outlook at Nashoba Valley.

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This Weekend in Littleton

Whimsical Watercolor Workshop (Whimsical Wonders Watercolor Workshop)
Glimmerbug Handmade Art
Wed, Oct 14 · 5:30 PM
Slow Drawing & Mindful Mark Making Class
Glimmerbug Handmade Art
Thu, Oct 15 · 10:00 AM
Witch's Woods operating night
Witch's Woods
Fri, Oct 16 · 6:30 PM
Keith Jacques
The Outlook at Nashoba Valley
Fri, Oct 16 · 8:00 PM
Jeeter Pop-Up | Collective Premium Cannabis (Billerica)
Collective Premium Cannabis Littleton
Sat, Oct 17 · 12:00 PM
Witch's Woods operating night
Witch's Woods
Sat, Oct 17 · 6:30 PM
Dave Powers
The Outlook at Nashoba Valley
Sat, Oct 17 · 8:00 PM
Crag Days (outdoor climbing)
MetroRock Littleton
Sat, Oct 17
Open Every Friday thru Sunday from October 3 to November 1, 2025 (INCLUDING Halloween Night)
Witch's Woods
Sat, Oct 17
Chuck Clough
The Outlook at Nashoba Valley
Sun, Oct 18 · 5:00 PM
Open Every Friday thru Sunday from October 3 to November 1, 2025 (INCLUDING Halloween Night)
Witch's Woods
Sun, Oct 18

Coming Up in Littleton

Open Every Friday thru Sunday from October 3 to November 1, 2025 (INCLUDING Halloween Night)
Witch's Woods
Mon, Oct 19
Kanha Halloween Take Over | Collective Premium Cannabis
Collective Premium Cannabis Littleton
Fri, Oct 23 · 4:00 PM
Witch's Woods operating night
Witch's Woods
Fri, Oct 23 · 6:30 PM
Walter Welch
The Outlook at Nashoba Valley
Fri, Oct 23 · 8:00 PM
Witch's Woods operating night
Witch's Woods
Sat, Oct 24 · 6:30 PM
Halloween Costume Party!
The Outlook at Nashoba Valley
Sat, Oct 24 · 8:00 PM
David Moore
The Outlook at Nashoba Valley
Sat, Oct 24 · 8:00 PM
Open Every Friday thru Sunday from October 3 to November 1, 2025 (INCLUDING Halloween Night)
Witch's Woods
Sat, Oct 24
Witch's Woods Costume Party
The Sunset Tiki Bar
Sun, Oct 25
Open Every Friday thru Sunday from October 3 to November 1, 2025 (INCLUDING Halloween Night)
Witch's Woods
Sun, Oct 25
Highmark Provisions Pop-Up | Collective Premium Cannabis
Collective Premium Cannabis Littleton
Mon, Oct 26 · 2:00 PM
Kanha Halloween Take Over | Collective Premium Cannabis
Collective Premium Cannabis Littleton
Mon, Oct 26 · 4:00 PM
Open Every Friday thru Sunday from October 3 to November 1, 2025 (INCLUDING Halloween Night)
Witch's Woods
Mon, Oct 26
Witch's Woods operating night
Witch's Woods
Fri, Oct 30 · 6:30 PM
Keith Jacques
The Outlook at Nashoba Valley
Fri, Oct 30 · 8:00 PM
Witch's Woods Halloween Night (final night per homepage caption)
Witch's Woods
Sat, Oct 31 · 6:30 PM
Dave Powers
The Outlook at Nashoba Valley
Sat, Oct 31 · 8:00 PM
Open Every Friday thru Sunday from October 3 to November 1, 2025 (INCLUDING Halloween Night)
Witch's Woods
Sat, Oct 31
Witch's Woods open (extended dates per Directions page)
Witch's Woods
Sun, Nov 1 · 6:30 PM
Witch’s Woods Haunted Hayride & Halloween Screampark
Witch's Woods
Sun, Nov 1
Open Every Friday thru Sunday from October 3 to November 1, 2025 (INCLUDING Halloween Night)
Witch's Woods
Sun, Nov 1
Witch's Woods open (extended dates per Directions page)
Witch's Woods
Mon, Nov 2 · 6:30 PM
Green Wednesday | Collective Premium Cannabis
Collective Premium Cannabis Littleton
Wed, Nov 25 · 12:00 AM
Thanksgiving Holiday Hours | Collective Premium Cannabis
Collective Premium Cannabis Littleton
Thu, Nov 26 · 12:00 AM
Black Friday Event | Collective Premium Cannabis
Collective Premium Cannabis Littleton
Fri, Nov 27 · 12:00 AM
Christmas Holiday Hours | Collective Premium Cannabis
Collective Premium Cannabis Littleton
Fri, Dec 25 · 12:00 AM
New Year’s Eve Holiday Hours | Collective Premium Cannabis
Collective Premium Cannabis Littleton
Thu, Dec 31 · 12:00 AM
Jimmy Fund Snow Challenge Fundraiser
Nashoba Valley Ski Area
Sun, Feb 7, 2027
Vertical Challenge – Free Race
Nashoba Valley Ski Area
Sun, Feb 7, 2027
Happy Valentine's Day
Nashoba Valley Ski Area
Sun, Feb 14, 2027 · 8:00 PM
Make your reservations at
Nashoba Valley Ski Area
Sun, Feb 14, 2027
Dave Powers The Outlook Restaurant 79 Powers Road, Westford FEB 13 2026
The Outlook at Nashoba Valley
Sun, Feb 14, 2027
Valentine's Day Event
Nashoba Valley Ski Area
Sun, Feb 14, 2027
Valentine’s Day Dinner
Nashoba Valley Ski Area
Sun, Feb 14, 2027
Chuck Alamo The Outlook Restaurant 79 Powers Road, Westford FEB 14 2026
The Outlook at Nashoba Valley
Mon, Feb 15, 2027
WAYNE WONG visits Nashoba
Nashoba Valley Ski Area
Fri, Feb 19, 2027
Tubing Park
Nashoba Valley Ski Area
Sun, Feb 21, 2027
12pm – 6pm ALL YOU CAN EAT BUFFET $48pp
Great Road Kitchen
Mon, Apr 5, 2027
420 Celebration | Collective Premium Cannabis
Collective Premium Cannabis Littleton
Tue, Apr 20, 2027 · 12:00 AM
Cinco de Mayo | Collective Premium Cannabis
Collective Premium Cannabis Littleton
Sat, May 1, 2027 · 12:00 AM

Venues in Littleton (8)

Witch's WoodsHaunted house
17 events
Collective Premium Cannabis LittletonVenue
15 events
The Outlook at Nashoba ValleyRestaurant
10 events
Nashoba Valley Ski AreaOutdoor Venue
8 events
Glimmerbug Handmade ArtArt studio
2 events
Great Road KitchenRestaurant
1 event
MetroRock LittletonRock climbing gym
1 event
The Sunset Tiki BarBar & Pub
1 event
Listings for Littleton, Massachusetts are compiled from public sources, each named with the site it came from and dated with the last time we read it. Details can change — confirm with the venue before you go. How we collect & verify.