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Massachusetts Walking Events Calendar 2026-2027

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Monthly updates for Massachusetts

Get new walking events (and updates) in your inbox every month.

Explore the best walking events in Massachusetts for 2026-2027! Our updated list features 212 great walks across the region. Find your next walk in Massachusetts below and join the walking community at these great events!

May 2027
May
1
Sa

Set the Pace 5K - Hingham

Road Race Walk
May
1
Sa

Run for Recovery - Boston

Road Race Walk
May
2
Su

Runway 5k - Northampton

Road Race Walk 3 mi
May
2
Su

Worcester Cinco 5K

Road Race Walk
May
16
Su

Runnin' for a Cause, Not from the Cops

Road Race Walk 5 km
May
29
Sa

Dennis Port 10K

Road Race Walk 5 km 10 km
May
30-31
Su - Mo

Vest Up for the Fallen

Walk 65 mi
June 2027
Jun
5
Sa

Finberg Family 5K Run/Walk

Road Race Walk 5 km
Jun
5
Sa

MammothMarch Boston

Trail Run Walk 20 mi
Jun
27
Su

Hanover Day 5K

Road Race Walk 5 km
July 2027
Jul
11
Su

Twice Is Nice 5 Mile Road Race

Road Race Walk
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