Islanders’ favorite walking routes

A group of ladies from the Camp Ground, Oak Bluffs, walk most summer mornings.
Walking, Path, Mom, Daughter, Lisa Brown
Photo by Lisa Brown

The Vineyard has hundreds of miles of beaches, trails and bikepaths to walk. Times contributor Kate Feiffer, who once walked all the way around Chappy in a single day, helped us round up some Islanders’ favorites.

One person we asked said, “My favorite walks will have to remain a secret.” Others were more forthcoming and all agree that avid hikers and Sunday strollers alike can criss-cross the Island through well-maintained trails in conservation, ancient ways, unsung paths, beaches, quiet roads, scenic towns and bike paths.

Dr. Louis Sullivan, Former U.S. Secretary of Health and Human Services

Dr. Sullivan and his wife Eve have walked together most mornings in the over 30 years they’ve been coming to the Vineyard, he told the Times in a story published in 2011. August mornings, you might see Dr. Sullivan strolling along the Beach Road bike path, in preparation for the Sullivan 5k race/walk held each August. This year is the 25th year the MV Hospital fundraiser has been held. “My wife, Eve, and I began daily walks more than 30 years ago for fitness and weight control. We began using our fitness time to share information about our lives and families, to discuss the problems of everyday life,” Sullivan told the Times.

Kara Taylor, Artist, West Tisbury

Kara Taylor admits that while some of her favorite hikes involve a bit of trespassing, she can access one spectacular hike from home that doesn’t require crossing anyone’s personal property. She calls it, “An incredible network of Land Bank, Nature Conservancy and Sheriffs Meadow.” Trails feed into each other on the north side of West Tisbury, and wind past Duartes pond, Blackwater Pond, Ripley’s Field and Wompesket. “This walk is quintessential Vineyard, and I love not having to get in my car to go there!” says Taylor.

Melissa Kagan, Tech consultant known as the “Mac Lady”

Poucha Pond in Chappaquiddick is one of Kagan’s favorite walks to take with family and friends. “It’s breathtaking and ideal for a family nature hike any time of year,” says Kagan.

Herb Foster, Retired Teacher

The Tiasquam Valley Reservation rates high among Foster’s favorite hikes. “I feel so alive when I’m there,” says the 85-year-old Foster. This Land Bank property peaks at 175 feet over sea level and is ideal for walkers that want their workout with a view.

Randi Baird, Photographer

Randi Baird and husband Philippe Jordi’s longtime Sunday morning routine takes them from their West Tisbury home to Stoney Hill Road through a Land Bank-owned property then down Holmes Hole Road. “We buy a newspaper and walk home,” says Baird.

Kara Shemeth Dekkers, Land Surveyor

Cedar Tree Neck is what Kara Shemeth Dekkers calls her “go-to walk.” Dekkers explains, “because of the varied topography and awe-inspiring views. The dogs love the hike and getting out to the beach to cool off before heading home. It’s not usually crowded either, which is nice.”

Susan Sigel Goldsmith,

Another vote for Tiasquam. Goldsmith appreciates the variety and diversity of trails and the windy twists and challenging hills. “You catch so many different pieces of nature,” she says, adding, “And you feel like you’re doing some improvements to the old physique.”

Dan Waters, Illustrator and poet

Waters’ favorite walks are ones that have some human element of surprise. For instance, he says, “there’s Christiantown Woods, where you suddenly come across a secret root cellar. Then there’s Fulling Mill Brook, where the path wanders past some old stone foundations and eventually crosses a stone bridge where the mill must have been. Finally there’s Great Rock Bight, with its humble and touching monument to Rebecca, Woman of Africa. It’s hard to say which of these is a favorite. It’s just good to be reminded that, even in the wilds of the Island, people lived whole long lives here before us.”

June Manning, Grandmother

Long time Islander June Manning wrote in: “My favorite walk is across Lighthouse Road, down Moshup Trail, along the beach under the Cliffs, and home again via Pilot’s Landing. Very peaceful, energizing, of course scenic, and intrinsically fascinating.”

Susan Savory, Children’s book specialist at Bunch of Grapes

Susan Savory moved to the Vineyard just three years ago, and picked Menemsha Hills as her favorite walk. Writes Savory: “I love the varied landscape. Three miles of trails that take you through wet marsh, wooded sections, flat open stretches and then gorgeous rocky coast. The vegetation is an amazing mix of oaks, beech trees, holly, pitch pine, beach plum and dune grass. Once you hit the dune cliffs you can see the Elizabeth Islands, Menemsha, Aquinnah, and on a clear day all the way to Noman’s Island. It has a little bit of everything, including hills to climb — it’s a perfect workout in a stunning place!”

Keith Dodge, Teacher, MVRHS

Keith Dodge’s after school routine includes a walk along the Oak Bluffs side of State Beach. “It’s nice to get your mail and go for a walk on the beach,” says Dodge.

Shelley Christiansen, Writer and real estate broker

A few years ago Shelley Christiansen discovered Fulling Mill Brook, in Chilmark, and was instantly drawn to the rugged woodsy terrain. “It reminded me of Sherwood Forest even though I’ve never been to Sherwood Forest,” said Christiansen, adding, “It reminds me of where I grew up. Just like there’s comfort food, there’s comfort woods.”

Heather Goff, Artist and computer programmer

Heather Goff often gets inspiration for her “daily sketches” from walks. “Most of the trails I walk because I can walk from my home or my parents’ house. You can walk all the way from middle road (near the old Silva Farm) to Great Rock Bite, for example. Or do wonderous loops on the new trails across from the Brookside Farm. I think my favorite place to walk, though, is Tradewinds because it is dog friendly and ever-changing with the seasons, probably doing a loop around Tradewinds, around Farm Pond, along the beach road and back through Harthaven.”

Alison Shaw, Photographer

“We like the big loop around Farm Pond,” she told us about her family outings with partner Sue Dawson and their kids Sarah and Jesse, “and also East Chop/Eastville. We park near the beach club, walk as far as the Nadler’s old house at the end of Eastville, and double back.”


Our social media friends had favorites, too:

“I really miss the walk in Vineyard Haven between Main Street and Pine, via Centre Street.” – Chris O.

“Love walking along South Beach when no one else is there!” – Susan M.

“Menemsha or Pay Beach [Oak Bluffs town beach] early in the morning when no one is there; then I leave when everyone else gets there and I am a hero for opening up a parking space. I like Vineyard Haven for window shopping!” – Helen M.

“Squib for the beautiful sunrise.” – Lori S.

“Lamberts Cove and Lucy Vincent…Best beaches on the planet.” – Julie G.


If you’re a runner take a look at some of the best routes to explore the Island courtesy of our friends at Great Runs