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Outdoor activities

in Winchester, MA

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

Hiking

Walk along the Original Boundaries of Boston

Sun, Dec 28 · 14:00 EST

Walk along the Original Boundaries of Boston

by Women Outdoors — Eastern Massachusetts Meetup

Horn Pond Nature Walk

Mon, Dec 22 · 10:30 EST

Horn Pond Nature Walk

by Active and Creative Women Only Friends-North Shore & Boston

Afternoon Hike on the Battle Road Trail - Lincoln MA

Fri, Jan 30, 2026 · 14:30 EST

Afternoon Hike on the Battle Road Trail - Lincoln MA

by Out And About in Northern MA and Southern NH

Jingle Trails: Music, Fun, and Fresh Starts! 🎵✨

Sat, Dec 20 · 08:45 EST

Jingle Trails: Music, Fun, and Fresh Starts! 🎵✨

by Blue Hills Hiking and Biking Club

Walking

Walk & Talk About Life's Big Questions

Sat, Jan 3, 2026 · 08:00 EST

Walk & Talk About Life's Big Questions

by The Board Walks – Boston

Nature Walk, Arnold Arboretum

Sat, Dec 20 · 10:00 EST

Nature Walk, Arnold Arboretum

by Nature Walking Group in Arnold Arboretum

New Years Day Walk -Back Bay, Boston (5 & 10 KM)

Thu, Jan 1, 2026 · 08:30 EST

New Years Day Walk -Back Bay, Boston (5 & 10 KM)

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

Weekly Multigroup Community Sunset Walk at Fresh Pond+optional dinner 3:15pm EST

Sun, Dec 21 · 15:15 EST

Weekly Multigroup Community Sunset Walk at Fresh Pond+optional dinner 3:15pm EST

by Boston Walking Meetup Group

Running

Boston Speed Dating For Serious Relationships

Sat, Dec 27 · 14:00 EST

Boston Speed Dating For Serious Relationships

by Heartlink Long Term Relations

Lazy Sunday Run and Coffee Social

Sun, Dec 28 · 08:00 EST

Lazy Sunday Run and Coffee Social

by Dashing Whippets Running Team - Boston Chapter

The Tuesday Track Workout

Tue, Dec 23 · 18:30 EST

The Tuesday Track Workout

by Informal Running Club's TMIRCE:BOS

Whippets Weekend Run - Boston Common

Sat, Dec 20 · 07:30 EST

Whippets Weekend Run - Boston Common

by Dashing Whippets Running Team - Boston Chapter

Cycling

Walk along the Original Boundaries of Boston

Sun, Dec 28 · 14:00 EST

Walk along the Original Boundaries of Boston

by Women Outdoors — Eastern Massachusetts Meetup

Learn to Fix Bikes at the Bicycle Institute of Technology!

Thu, Jan 8, 2026 · 18:30 EST

Learn to Fix Bikes at the Bicycle Institute of Technology!

by North Shore Bicycling For Fun

Meet & Ride at Revolution Hall

Wed, Dec 24 · 18:00 EST

Meet & Ride at Revolution Hall

Thursday Night Regiment (Run Club)

Thu, Dec 18 · 18:00 EST

Thursday Night Regiment (Run Club)

by East Regiment Events

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