Community Events · Massachusetts
Find your next ride,
walk, or roll.
134 events
Get these by emailTuesday · October 27
66 AMto 8 AM
Group Ride · Rec · 24 miles
Speedy Croissant Women/NB Ride (24)
6 AM · Charles River Wheelers · Minuteman Bikeway Trailhead, Alewife · 2.3 mi
Women and nonbinary
7:45 AM
Talk / Panel
Moving Together Conference 2026
7:45 AM · UMass Transportation Center · Sheraton Boston Hotel · 2.3 mi
PaidRegistration req’dAdvocacy
9 AMto 11 AM
Walking Tour
Tuesday Morning Walk for Women Over 40
9 AM · Boston Women over 40 Walking Group · 351 Boylston St, cnr with Arlington Street, Boston, MA · 2.5 mi
FreeWomen and nonbinaryBeginner-friendly
4 PMto 5 PM
Group Ride · Easy · 2 miles
Trek or Treat Ride on the Bruce Freeman Rail Trail
4 PM · Minuteman Bike Share · West Concord bike share station (next to West Concord commuter rail) · 16 mi
FreeFamily-friendlyBeginner-friendly
Wednesday · October 28
510 AMto 2 PM
Group Ride · Rec · 30 and 40 miles
Wednesday Wheelers
10 AM · Charles River Wheelers · Varies Weekly · 7.9 mi
12 PMto 1 PM
Walking Tour
Snail walk with Mary P
12 PM · Boston Walking Meetup Group · 35 Brookford St, Cambridge, MA · 2.2 mi
FreeBeginner-friendlyFamily-friendly
Thursday · October 29
510 AMto 1 PM
Group Ride · Rec · 34 miles
Truant Thursday to Honeypot
10 AM · Charles River Wheelers · Gerow Park · 16 mi
10 AMto 11:30 AM
Walking Tour
English "Walk and Talk" Time! (outdoors)
10 AM · Thomas Crane Public Library · Olmsted Lawn · 10 mi
FreeFamily-friendly
10 AM
Group Ride · Rec · 20 miles round trip
Cycle with MIT Club of Boston
10 AM · Hayward Zwerling / MIT Club of Boston · Thorndike Field Park Parking Lot · 2.8 mi
Free
Friday · October 30
5All day
Community Challenge
Walk/Ride Day — October 2026
Green Streets Initiative · Wherever you are in Massachusetts · 2.7 mi
FreeFamily-friendlyBeginner-friendly
7 AMto 9 AM
Group Ride · Rec · 20 miles
Praline Croissant WNB (20)
7 AM · Charles River Wheelers · Minuteman Bikeway Trailhead – Alewife · 2.3 mi
Women and nonbinary
12 PMto 2 PM
Walking Tour
Tour of Charlesgate
12 PM · Emerald Necklace Conservancy · The Grove, Charlesgate · 2.7 mi
FreeRegistration req’d
Saturday · October 31
16All day
Community Challenge
Rideshare Month Trivia Challenge
Neponset Valley TMA · Online, all month · 13 mi
Free
7 AMto 9:30 AM
Group Ride · Rec · 2 hours
Landry's Braintree All-Levels Saturday Road Ride
7 AM · Landry's Bicycles · Landry's Braintree · 11 mi
No-dropFreeRegistration req’d
8 AMto 12 PM
Group Ride · Rec · 40 miles
B2C Halloween Ripper 40-Mile Challenging Ride
8 AM · Bike to the Sea · B2C Bike Kitchen, 158 Canal St., Malden, Massachusetts, 02148 · 3.8 mi
PaidRegistration req’d
9 AMto 2 PM
Group Ride · Moderate · 19 or 34 miles
Women's/Nonbinary Halloween Spooktacular Ride
9 AM · Charles River Wheelers · AERO Coffee Roasters · 26 mi
No-dropWomen and nonbinary
9:45 AMto 11:45 AM
Walking Tour
Saturday Group Walk: Newton Centre, MA (10 & 5KM Walk options)
9:45 AM · Walk 'N Mass Volkssport Club · 330 Homer St, Newton, MA · 5.7 mi
PaidFamily-friendly
10 AM
Group Ride · Rec
Greater Boston NEMBA Family Halloween Ride
10 AM · Greater Boston NEMBA · Elsie Turner Field, Rock Meadow Playground · 5.8 mi
10 AMto 10:45 AM
Walking Tour
Step into History Walking Tour
10 AM · Lowell National Historical Park · Lowell National Historical Park Visitor Center · 21 mi
10 AMto 2 PM
Other
Great Commuter Challenge: Halloween
10 AM · Bikes Not Bombs · Bikes Not Bombs · 4.1 mi
FreeFamily-friendly
10 AMto 12:30 PM
Walking Tour
Nature Walk at Arnold Arboretum
10 AM · Nature Walking Group in Arnold Arboretum · Forest Hill Rd, Boston, MA · 5 mi
FreeBeginner-friendlyFamily-friendly
11 AM
Group Ride · Easy
What's Scarier Than Mass Ave? Halloween Costume Group Ride
11 AM · Boston Cafe Bikers · Central Square, Cambridge, MA · 0.7 mi
No-dropBeginner-friendlyFamily-friendlyFree
12:30 PMto 2:30 PM
Walking Tour
Walking Tour: Allston Under Construction
12:30 PM · Allston-Brighton Housing Action (ABHA) · Old CVS site, 1270 Commonwealth Ave · 2.1 mi
Beginner-friendlyFamily-friendly
1 PMto 3 PM
Walking Tour
Tour of Charlesgate
1 PM · Emerald Necklace Conservancy · The Grove, Charlesgate · 2 mi
FreeRegistration req’d
2 PMto 3:30 PM
Walking Tour
Peters Hill Tour
2 PM · Arnold Arboretum of Harvard University · Poplar Gate · 5.4 mi
FreeRegistration req’d
3 PM
Group Ride · Easy
October Bike Ride
3 PM · Bike Together Waltham · Waltham City Hall · 6.4 mi
FreeBeginner-friendlyFamily-friendly
Sunday · November 1
310 AMto 11:30 AM
Walking Tour
Awash in Color - a fall foliage walking tour
10 AM · Friends of Mount Auburn Cemetery · Mount Auburn Cemetery, 580 Mount Auburn St., Cambridge, 02138, United States · 1.8 mi
Registration req’d
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