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Outdoor activitiesin Littleton, Massachusetts

Discover outdoor activities in Littleton with Meetup. Whatever your interest, Meetup helps you connect with like-minded people.

Hiking

Winterberry Way, Taylor Way and Harry Way Loop and Medusa Brewing!

Hosted by: Hikes and Brew’s and fun activities meetup group

17 going
Free
Winterberry Way, Taylor Way and Harry Way Loop and Medusa Brewing!

northern half of the skyline trail from Winchester

Hosted by: Hike the Middlesex Fells

10 going
Free
northern half of the skyline trail from Winchester

northern half of the skyline trail from Winchester

Hosted by: Hike the Middlesex Fells

3 going
Free
northern half of the skyline trail from Winchester

Assabet River Walk

Hosted by: Make Friends As An Adult

2 going
Free
Assabet River Walk

Cycling

2025 Wednesday moderate Fitness Ride

Hosted by: Greater Boston and New England Area Cycling

1 going
Free
2025 Wednesday moderate Fitness Ride

S&W Wednesday Night Rides

Hosted by: Granite State Wheelers bicycling club

1 going
Free
S&W Wednesday Night Rides

2025 Monday Intermediate / Fast Training Ride

Hosted by: Greater Boston and New England Area Cycling

1 going
Free
2025 Monday Intermediate / Fast Training Ride

Rescheduled - Biking on the Bruce Freeman Rail Trail - Chelmsford MA.

Hosted by: New England Over 50 Hiking Group

20 going
Free
Rescheduled - Biking on the Bruce Freeman Rail Trail - Chelmsford MA.