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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

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

Morning Hike - North Reservoir

Hosted by: Hike the Middlesex Fells

18 going
Free
Morning Hike - North Reservoir

Rick’s Ramble: West Boylston Rail Trail

Hosted by: Fellowship of the Tortoise

12 going
Free
Rick’s Ramble: West Boylston Rail Trail

northern half of the skyline trail from Winchester

Hosted by: Hike the Middlesex Fells

4 going
Free
northern half of the skyline trail from Winchester

Walking

BreakthroughT1D Walk - Boston

Hosted by: Type 1 Diabetes Fighters

1 going
Free
BreakthroughT1D Walk - Boston

Group Walk: Concord, MA (5 and 10K Walk Options)

Hosted by: Walk 'N Mass: Walk for Fun, Fitness, Friendship in MA & RI

13 going
Free
Group Walk: Concord, MA (5 and 10K Walk Options)

East Boston Camps and Gould Road Loop Trail

Hosted by: Rockingham Outdoors and More...

20 going
Free
East Boston Camps and Gould Road Loop Trail

Weekly Multigroup Community Sunset Walk at Fresh Pond+optional dinner 5:30pm EDT

Hosted by: Boston Walking Meetup Group

5 going
Free
Weekly Multigroup Community Sunset Walk at Fresh Pond+optional dinner 5:30pm EDT

Cycling

2025 Wednesday moderate Fitness Ride

Hosted by: Greater Boston and New England Area Cycling

Be the first
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

Be the first
Free
2025 Monday Intermediate / Fast Training Ride

Fall Foliage Series: Connecticut River Scenic Byway

Hosted by: Boston Countryside Cruisers

2 going
Free
Fall Foliage Series: Connecticut River Scenic Byway