Oak Bluffs
Walking Events Calendar near Oak Bluffs 2026-2027
Monthly updates for Oak Bluffs
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Explore the top walking events near Oak Bluffs for 2026-2027! We've gathered 21 great walks in the area. Check out our detailed list below to find your next local walk.
July 2026
Walkers can take part in the full 5K on Martha's Vineyard in West Tisbury, with wheelchair, handcycle and duo team options and a separate 400 m kids fun run. The event starts at 401 Old County Rd and takes place alongside the running races.
August 2026
Walkers can join a 5K route on beautiful Cuttyhunk Island in Gosnold MA, enjoying an outdoor community event alongside the running races. All ages are welcome and proceeds support Cuttyhunk First Aid and Rescue and Cuttyhunk CAN.
Walkers can take part in the community Run/Walk covering 5K (3.2 miles), starting at 15 Island Inn Rd, Oak Bluffs, MA. The scenic Martha's Vineyard course welcomes all fitness levels and emphasizes community and wellbeing.
Walkers can use the 5K route that starts and ends at the Farm Institute in Katama, follows Edgartown Bay Road past South Beach, and returns along the bike path. The course is well marked and on site registration and bib pickup are available; park..
Walkers follow a 5K route starting at Washington Park on a USATF certified course through East Chop with views of Nantucket Sound. Strollers and leashed pets are welcome and asked to stay toward the back, and bib and T shirts are available for pi..
September 2026
Walkers can choose a 5K route starting in Ocean Park that winds through Oak Bluffs streets circling the harbor and East Chop with views of Vineyard Sound. A 1 mile fun walk for kids starts from the Summercamp Hotel and welcomes strollers and..
Walkers can take part in the 5k (scenic 3.1 mile) route around Sandwich Marina and the beach, starting and finishing at Stop & Shop Plaza, 65 Rt 6A, Sandwich MA. Walkers go alongside the running race; runners leave the start first.
Walkers follow a 1 mile route in Nantucket starting at 33 Bartlett Farm Road at Bartletts Farm, with bib and t shirt pick up available the day before and on event day. The walk runs alongside the races and offers a virtual option.
The event features a 5k walk in Buttonwood Park, New Bedford, meeting at the corner of Lake Street and Buttonwood Street behind Lawler Library. Race packet pickup, post walk breakfast, music, honor beads, and same day registration are available f..
October 2026
Walkers can take part in the 5k either in person or virtually alongside running races, with a free Kid's Dash for ages 8 and under. The event raises funds for the Patient and Caregiver Fund to support patients and families.
Walkers can do the in person or virtual 5K from 120 Main Street in Buzzards Bay, with parking at the Buzzards Bay Recreation Area lot. The in person USATF course has professional chip timing and bib pickup a few steps down the road at 120 Main St..
November 2026
Walkers follow a 5K out and back route from Cushman Park on Green St to Fort Phoenix, passing the marina and a water stop. Bib pickup is at 56 Bridge Street the day before and morning of the event, with police and volunteers staffing crossings.
The event offers a community 5k walk starting at The Dennis Inn on Scarsdale Road in Dennis, MA, on a road course. Parking is at the Dennis Playhouse and the walk is held alongside the 5k run as a community benefit.
April 2027