Did you know there are over two hundred miles of public trails on Martha’s Vineyard? There are so many that there is even have an app for it! Whether you’re taking a scenic stroll, walking the dog, hiking, or biking, the Island has it all. We’ve included a list below of several trails that the whole family can enjoy, even with a stroller!
Though strollers are great options for friends and families with children who are not quite ready to explore the outdoors on foot, we know trying to pinpoint what trails are stroller-friendly can be difficult, so we've pulled together this super simple list of over ten trails all over the Island. We hope you have fun exploring the most popular stroller-friendly trails on Martha’s Vineyard with this hand-curated list!
Sheriff’s Meadow Sanctuary. Just outside downtown Edgartown sits this beautiful getaway that lives up to its name. Sheriff’s Meadow Sanctuary is an 18-acre property owned by the Sheriff’s Meadow Foundation. Since April 2021, the Sanctuary has been hosting a storybook walk with the Edgartown Public Library. Each month, a new children’s book is chosen and pages are placed along the Brooks Trail, starting off of Plantingfield Way. The storybook walk is roughly a half-mile, but the scenic views of Ice Pond and the ocean might keep you walking for longer.
Nat’s Farm. If you’re in the West Tisbury area, Nat’s Farm is a great place for the family and is very stroller-friendly. Located off Old County road, the farm covers 56 acres of meadow, pasture, field, and oak woods. A wide and flat trail loops around a large northern pasture that houses a handful of horses from the Martha’s Vineyard Horse Center. There are even a few activities and puzzles for all members of the family to enjoy while on their walk!
Island Folk Pottery Sculpture Trail. This trail might not be the best if you have a wide stroller but is worth checking out in any case. Located in Chilmark off Marion’s Way, children will especially love this one for the enchanting atmosphere. Fairy houses, dragons, tree spirits, and other characters can be found along the half-mile trail. The trail was made by the owners of Island Folk Pottery, Bill O'Callaghan, and Heather Goff. At the end of your walk, consider checking out their pottery studio. You may just bring a little magic home with you!
Wallen, Preston, and Shands Preserve. Looking for some stunning ocean views? This loop trail in Aquinnah will not disappoint! Atop the Gay Head Cliffs, this trail connects the Aquinnah Cultural Center, Moshup Beach, and the Land Bank’s Aquinnah Headlands Preserve. The trail itself is flat with a wide path that shouldn’t give you much trouble. It’s also dog-friendly!
Blackwater Pond Reservation. This trail is located off of Lambert’s Cove Road in West Tisbury and follows four different ponds: Blackwater Pond, Northern Duarte’s Pond, Southern Duarte’s Pond, and Turtle Pond. The Blackwater Pond Reservation trail is considered very easy with a very flat and wide path that narrows once you get into the woods. There is a beautiful wooden bridge that crosses Duarte’s Pond, and if you get there in early spring, you might even catch hundreds of lily’s blooming on the water! This is a perfect spot for a scenic stroll and a picnic with the family.
Sepiessa Point Reservation. This trail is located in West Tisbury off of Edgartown-Vineyard Haven Road and is best if you have a buddy. Towards the beginning of the trail, there is a short segment where a stroller will have to be carried, but once you get past that it is smooth sailing! Sepiessa takes you out to the stunning Tisbury Great Pond and if you’re lucky, you may catch a glimpse of some swans, ducks, plovers, and even ospreys!
Quansoo Farm. Located on Tisbury Great Pond and Black Point Pond, Quansoo Farm in Chilmark has a trail that follows the perimeter of the property and accompanying Quansoo Preserve. This trail is fairly wide and has a truly unique landscape, ranging from meadows, fields, and woods filled with gnarled oaks. This walk is both breezy and breathtaking and definitely worth the trip!
West Chop Woods. Less than a mile and a half from downtown Vineyard Haven, the West Chop Woods offers over one and a half miles of marked walking trails. If you’re around in the springtime, this is the perfect spot to catch a glimpse of a rare pink Lady Slipper!
Huckleberry Barrons. If you’re looking for a short and peaceful experience, Huckleberry Barrons in Katama is a great loop trail with several areas to rest and enjoy the scenery. The loop is approximately a half-mile and is perfect for hot sunny days. This wooded trail has lots of nice shade and is pet-friendly!
Fulling Mill Brook. Located in Chilmark, the Fulling Mill Brook Preserve is a very peaceful walk with a variety of local songbirds to admire. The main trail will keep you on easy terrain through woods and meadows. Be warned, the boardwalks are not stroller-friendly!
Great Rock Bight. This loop around Marl Pond consists of a very easy trail that is perfect for strollers. The trail follows the perimeter of several ponds into the forest, and the land is very well kept. The ponds are exclusively home to the rare clam shrimp, and one of the ponds is shaped like a heart! If you plan on bringing a stroller, we don’t recommend taking the trail all the way down to the beach.
Huge thanks to everyone that shared their photos with us: Kaylan Look, Mikey Waters, Guinevere Rebello, Simma Rashba, and Emily Avakian.
Visit Martha's Vineyard
Loving Martha's Vineyard is the easiest thing in the world to do.