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Outdoor activities

in Wellesley Hills, MA

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

Hiking

Holliston First Night Rail Trail Walk - Dec 31 - 5:00 PM to 8 PM

Wed, Dec 31 · 5:00 PM EST

Holliston First Night Rail Trail Walk - Dec 31 - 5:00 PM to 8 PM

by Fellowship of the Tortoise

Afternoon Hike on the Battle Road Trail - Lincoln MA

Fri, Jan 30, 2026 · 2:30 PM EST

Afternoon Hike on the Battle Road Trail - Lincoln MA

by Out And About in Northern MA and Southern NH

Crystal Springs, Virginia Wood and MWRA Reservoir

Fri, Jan 2, 2026 · 10:00 AM EST

Crystal Springs, Virginia Wood and MWRA Reservoir

by Hike the Middlesex Fells

Narrow-Gauge Rail Trail - Part 2

Sun, Jan 4, 2026 · 12:00 PM EST

Narrow-Gauge Rail Trail - Part 2

by The Exploring Group

Walking

Walk & Talk About Life's Big Questions

Sat, Jan 3, 2026 · 8:00 AM EST

Walk & Talk About Life's Big Questions

by The Board Walks – Boston

Nature Walk, Arnold Arboretum

Sat, Dec 27 · 10:00 AM EST

Nature Walk, Arnold Arboretum

by Nature Walking Group in Arnold Arboretum

Saturday Group Walk: Newton Centre, MA (10 & 5KM Walk options)

Sat, Jan 10, 2026 · 10:15 AM EST

Saturday Group Walk: Newton Centre, MA (10 & 5KM Walk options)

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

Wednesday walks: Freedom Trail, Boston (5 & 10 KM)

Sun, Dec 28 · 10:15 AM EST

Wednesday walks: Freedom Trail, Boston (5 & 10 KM)

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

Running

Lazy Sunday Run and Coffee Social

Sun, Dec 28 · 8:00 AM EST

Lazy Sunday Run and Coffee Social

by Dashing Whippets Running Team - Boston Chapter

Easy Miles - Boston Common

Fri, Dec 26 · 6:45 AM EST

Easy Miles - Boston Common

by Dashing Whippets Running Team - Boston Chapter

Whippets Weekend Run - Boston Common

Sat, Dec 27 · 7:30 AM EST

Whippets Weekend Run - Boston Common

by Dashing Whippets Running Team - Boston Chapter

Easy Run (5–10km/3–6 miles) + Brunch + Networking

Sat, Dec 27 · 9:30 AM EST

Easy Run (5–10km/3–6 miles) + Brunch + Networking

by Founders Running Club :: Boston

Cycling

Hike: Blue hills 4-5 miles hike at good pace

Thu, Dec 25 · 9:00 AM EST

Hike: Blue hills 4-5 miles hike at good pace

by Blue Hills Hiking and Biking Club

Boston Code and Coffee @ CIC

Sat, Jan 10, 2026 · 12:00 PM EST

Boston Code and Coffee @ CIC

by Boston Code and Coffee

Indoor Pool Practice w/Living Root Dragon Boat Club

Tue, Jan 6, 2026 · 6:30 PM EST

Indoor Pool Practice w/Living Root Dragon Boat Club

by Living Root Dragon Boat - Boston

Brookline to Roxbury High Fort / Highland Park Sunday Morning Urban Walk

Sun, Dec 28 · 8:30 AM EST

Brookline to Roxbury High Fort / Highland Park Sunday Morning Urban Walk

by Mosaic Jewish Outdoor Club of Massachusetts

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