Outdoor activities in Littleton, Massachusetts

Andover Trail Hike along Merrimack River

Hosted by: The Exploring Group

Sat, Sep 6 · 9:30 AM EDT

16 going

Andover Trail Hike along Merrimack River

MAMA Hike - Beaver Brook - Hollis, NH

Hosted by: 4 Seasons Hiking Group

Mon, Sep 8 · 9:30 AM EDT

20 going

northern half of the skyline trail from Winchester

Hosted by: Hike the Middlesex Fells

Sun, Sep 7 · 9:00 AM EDT

8 going

Sun, Sep 28 · 11:00 AM EDT

northern half of the skyline trail from Winchester

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

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

14 going

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

Walking

Sat, Sep 6 · 11:00 AM EDT

Sheldrick Forest Preserve - Nature Conservancy First EVENT!

Hosted by: Southern New Hampshire Nature Walks and Conservation Group

Sat, Sep 20 · 10:00 AM EDT

Sheldrick Forest Preserve - Nature Conservancy First EVENT!

Wayland Family Nature Walk

Hosted by: Wayland Nature Walks

Sat, Sep 20 · 8:00 AM EDT

Bolton Lime Quarry and Kiln Loop ON LEASH

Hosted by: Walk and Wags Dog Hiking

9 going

Bolton Lime Quarry and Kiln Loop ON LEASH

Weekly Multigroup Community Sunset Walk at Fresh Pond+optional dinner 6:00pm EDT

Hosted by: Boston Walking Meetup Group

Sun, Sep 7 · 6:00 PM EDT

4 going

Weekly Multigroup Community Sunset Walk at Fresh Pond+optional dinner 6:00pm EDT

Running

Wed, Sep 10 · 6:45 AM EDT

5-6 Mile Run Starting from Medford Square

Hosted by: Medford Square Runners

Tue, Sep 16 · 6:00 PM EDT

5-6 Mile Run Starting from Medford Square

Marlborough Lions Club Couch to 5k 10 Week Program Week 3!

Hosted by: Marlborough Couch to 5K

2 going

Sat, Sep 27 · 10:00 AM EDT

Marlborough Lions Club Couch to 5k 10 Week Program Week 3!

Run & Chug: Saturday Morning Longer Run

Hosted by: Boston Fun Run

4 going

Marlborough Lions Club Couch to 5k 10 Week Program Week 1!

Hosted by: Marlborough Couch to 5K

Sun, Sep 7 · 8:00 AM EDT

2 going

Marlborough Lions Club Couch to 5k 10 Week Program Week 1!

Cycling

Wed, Sep 10 · 5:45 PM EDT

2025 Wednesday moderate Fitness Ride

Hosted by: Greater Boston and New England Area Cycling

2025 Monday Intermediate / Fast Training Ride

Hosted by: Greater Boston and New England Area Cycling

Mon, Sep 8 · 5:45 PM EDT

Wed, Sep 10 · 5:00 PM EDT

2025 Monday Intermediate / Fast Training Ride

S&W Wednesday Night Rides

Hosted by: Granite State Wheelers bicycling club

Greater Boston ride - read for the options

Hosted by: North Shore Bicycling For Fun

Sun, Sep 7 · 9:00 AM EDT

15 going

Greater Boston ride - read for the options

Suggested groups