Mutts’ Vacation on Martha's Vineyard, Massachusetts
- Luie Boone
- 13 hours ago
- 11 min read
This travel spot is featured in our sixth blog series, Mutts Mingle.
When Luie Boone heard his hoomans were planning a vacation to Martha’s Vineyard, Massachusetts, he immediately thought of Martha Stewart because his hooman sister Rachel talks about her like she’s family. Unfortunately, no Martha.
Then he heard about the strange glowing lights over the coast, and suddenly this trip felt a lot more interesting. Locals have reported glowing orbs hovering or darting across the sky, sometimes during the day, sometimes at night, moving in ways that don’t really make sense.
It gets even weirder. Some fishermen say their compasses go haywire when the lights show up, and others swear the lights follow their boats before disappearing.
So yes, no Martha… but possibly something a little otherworldly, and Luie Boone is absolutely paying attention.
Martha’s Vineyard, Massachusetts, might have its mysteries, but it’s also an easygoing, dog-friendly island that Luie Boone can get behind. With scenic beaches, walking trails, and charming towns, it’s the kind of place where your pup is part of the experience. Each area has its own personality, with plenty of dog-friendly spots to stay, eat, and explore together.
Getting to Martha’s Vineyard with your dog is part of the adventure, especially by ferry from Woods Hole, Massachusetts. Luie Boone is already imagining himself on deck, ears in the wind, as Captain Luie Boone. He'll need a hat to make it official.
Dogs are welcome on most ferries as long as they’re leashed or in a carrier, and many boats have outdoor areas where pups can take in the fresh sea air. The Steamship Authority runs the main route to Vineyard Haven and Oak Bluffs.
There's also the Seastreak Ferries, which offers seasonal service from New Bedford with dog-friendly spaces. Either way, it's always a good idea to bring water, a leash, waste bags, and maybe a towel for sandy paws. Booking ahead helps too, especially in the summer when everyone else has the same pawsome idea.
Once you arrive on Martha’s Vineyard, Massachusetts, the adventure really begins. Luie Boone can already tell this is the kind of place where every walk turns into something new.
Each of the island’s six towns has its own mix of scenic paths, beaches, and dog-friendly spots, so you and your pup can keep exploring without it ever feeling the same. From historic harbors to quiet stretches of sand and tucked-away trails, there’s always another corner worth checking out.
In Edgartown, you can stroll along the scenic harbor, where the marina and pier set the scene for an easy, breezy walk. Luie Boone is already imagining a slow pace here, taking in every smell along the water.
Dogs are welcome at Chappy Point Beach, where Katama Bay meets Edgartown Harbor. It’s a calm, open spot for a leashed walk, and there’s even a working shellfish nursery nearby that helps support the island’s waters.
For dining, 19 Raw Oyster Bar offers a seasonal patio where pups can hang out alongside their hoomans.
The menu leans towards seafood with a bistro feel, and Luie Boone is very interested in the fact that there’s a beer named after a dog named Maya Mae.
The next town, Oak Bluffs, is known for its colorful Gingerbread Cottages and lively harbor, and Luie Boone is already intrigued by the name alone. It feels like the kind of place where every corner looks a little different from the last.
Dogs are welcome on the walking paths and around the Campground trails, making it easy to wander and take it all in. Along the harbor, Lobsterville Bar and Grille is a go-to spot for fresh seafood and drinks, with a dog-friendly open-air deck right on the water. Luie Boone would recommend timing your visit with sunset.
Vineyard Haven serves as the island’s main ferry port, so it’s often the first stop and an easy base for exploring. Luie Boone appreciates a place with constant arrivals, which means new smells and new people. Leashed dogs can walk along the harbor boardwalk, making it a simple and scenic spot to wander.
The Black Dog Bakery Cafe, in Vineyard Haven, doesn’t allow dogs inside, but you can grab something to go and settle in at an outdoor table with your pup. They serve breakfast, lunch, and plenty of baked goods, and they even have treats for dogs. Luie Boone considers that a very important detail.
West Tisbury offers a quieter, more laid-back side of the island, with open spaces and trails that feel a little more off the beaten path. Luie Boone likes this kind of pace, less hustle, more sniffing.
Lambert’s Cove Beach is one of the highlights, with clear blue water, soft sand, and calm conditions that make it feel extra peaceful. There’s even a section where dogs can be off leash, which Luie Boone finds very important. Access can be limited during peak times, but visiting early in the day, later in the evening, or during the off-season makes it easier to enjoy. Luie Boone would personally vote for sunset.
Chilmark brings a more rugged, coastal feel, with rolling hills, ocean views, and quiet roads lined with small farm stands. Luie Boone thinks this is the kind of place where you slow down without even trying.
It’s also home to Menemsha, a classic fishing village that feels straight out of a postcard. Right in the middle of it is Menemsha Galley, a 76 year old home cooking eatery known for simple, fresh food and a super relaxed vibe. Grab something to go, maybe even a soft serve, and wander the harbor with your pup. Luie Boone is very supportive of any plan that involves food and a waterfront walk.
If you make your way to the western edge of the island, Aquinnah feels like stepping into a completely different world. Known for its striking red clay cliffs and unforgettable sunsets, it’s the kind of place that makes you stop and just take it all in. Luie Boone is doing a full pause here.
Leashed dogs can walk along the cliffs, taking in the views while sticking to the designated areas. It’s not just beautiful, it’s meaningful too. Aquinnah is home to the Aquinnah Wampanoag Tribe, the original settlers of Martha’s Vineyard, and the Aquinnah Circle Cultural District offers a chance to learn more about their history and culture.
Martha’s Vineyard is the kind of place where dogs are treated like part of the family, and Luie Boone noticed that right away. With a little planning, keeping water handy, and following local leash rules, you and your pup can move easily from beaches to trails to town without missing a beat. It’s the kind of trip where you don’t have to leave your dog behind, and honestly, you wouldn’t want to.
Paws Rest Here
Luie Boone paw-selected this perfect vacation rental for your stay on Martha’s Vineyard, Massachusetts. Check it out below!
Rental Name: KAT VDAN-107
This rental has 4 bedrooms with 5 beds and 3 baths.
Photos by pointbrealty.com
It features the following amenities:
On Katama Bay waterfront
Set on over an acre
Large deck off the living and dining room
Second floor master bedroom, with its own private deck
Expansive front and backyards
Two lounge chairs
Propane grill
Enclosed outside shower
Seven beach chairs
Private boardwalk across the beach grass
Steps that lead right to the water
Kayak and a canoe
What does Luie Boone think of this rental? He woofed:
My hoomans picked a place with over an acre, which means unlimited zoomies in every direction. There’s also a private boardwalk through beach grass that leads straight to the water, and I already know I will be sprinting down it like it’s my personal runway. They keep talking about a big deck facing the ocean where they’ll watch sunsets. I will also be there, watching very closely for any dropped food. Inside, there are huge windows for proper monitoring and multiple bedrooms that I plan to rotate through for naps. Everything sounds extremely well set up for me. I also learned something important. There used to be a bird here called the Heath Hen that lived in these same coastal grasslands. It spent its time out in the open, just existing confidently, which I respect. It’s not around anymore, which is really unfortunate. When I visit, I will honor the Heath Hen properly. Fast runs through the grass, a few proud pauses, taking it all in. I haven’t even been yet, but I can already tell… this place is going to be very, very good.
Read more about Heath Hen here:
Paws Venture Here
Luie Boone sniffed out and dug up these local gems for you to check out while vacationing to Martha’s Vineyard, Massachusetts!
John Butler’s Mudhole
Back in the 1850s, this quiet spot off Planting Field Road in Edgartown was home to an old ice pond filled with wildlife. Muskrats, turtles, and swans lived here, and in the winter, people even cut blocks of ice to store for the warmer months. Luie Boone thinks that’s a lot of effort for something that melts.
Everything changed when Henry and Elizabeth Hough stepped in. After selling magazine rights to a book in 1958, they used the money to buy the land and protect it from development when no one else would.
Their efforts led to the creation of Sheriff’s Meadow Foundation, and this area became its very first protected property. Today, visitors and their pups can walk the trails and take in the landscape that was saved. The pond itself is now known as John Butler’s Mudhole, and while it once lived up to that name, it’s now easier to explore thanks to a loop trail and viewing platforms. Luie Boone is still a little disappointed there’s less mud than advertised.
Waskosim’s Rock
Long before Martha’s Vineyard was an island, glaciers shaped the land and left behind massive stones like Waskosim’s Rock. This huge granite boulder has been here for thousands of years, and Luie Boone immediately respects anything that old and still standing.
Over time, it became a natural gathering place, first for the Wampanoag people and later for settlers and visitors who found meaning in the landscape. Today, it still draws people in with its views and quiet presence.
As you explore the roughly three miles of trails with your pup, you’ll pass through woods, wetlands, and open fields. Along the way, you can spot remnants of early farming like stone walls and old foundations that still mark the land. There’s even a herd of goats that help maintain the fields, which Luie Boone finds both confusing and impressive. He'll try to befriend the goats and see if they'll teach him their ways.
Island Spirit Kayak
Island Spirit Kayak lets you and your pup get out on the water together in Oak Bluffs, which Luie Boone finds both exciting and slightly concerning for balance reasons. You can rent your own kayak or join a guided tour, depending on how adventurous you’re feeling.
Their most popular option is a two-hour guided paddle that takes you along some of the island’s best beaches and wildlife spots. There are also sunrise and sunset tours, plus a night “Glow Board” experience where lights under the boards let you see into the water below. They even have dog life jackets in all sizes, which feels important. Luie Boone will be participating, but if his fat tooshie tips the kayak over, he will simply act like that was part of the plan.
Follow the Lighthouses
If you’re looking for a way to explore the island, following Martha’s Vineyard’s five historic lighthouses is a solid plan. Luie Boone considers this a very official sightseeing mission.
Start with the Edgartown Lighthouse, which is one of the most scenic. It's set right on the harbor with a nearby beach, where you and your pup can walk and take it all in.
From there, Gay Head Lighthouse rises above the red cliffs in Aquinnah, with views that feel completely unreal and a history tied closely to the Wampanoag community. Then, in Oak Bluffs, East Chop Lighthouse sits up on a hill and opens for sunset visits in the summer, while West Chop Lighthouse in Vineyard Haven stands watch over the harbor, visible from the road and water. It’s not open to the public, but Luie Boone says a respectful drive-by still counts.
Cape Poge Lighthouse is the most remote of the five, tucked away and known for being moved more than once to stay ahead of the shoreline. Getting there feels like its own little adventure. Please note that dogs aren’t allowed inside the lighthouses, but you can get close enough for a very solid photo. Luie Boone plans to visit all five and consider himself extremely accomplished afterward.
Manuel F. Correllus State Forest
Right in the center of Martha’s Vineyard sits this massive forest, and Luie Boone is already planning full exploration mode. It started as a conservation effort for the Heath Hen back in 1908, a bird that once lived across the island.
Even though the Heath Hen is no longer around, the forest has grown into a huge recreational space with miles of trails for hiking and biking. It’s the kind of place where you can wander for a while and still feel like you’ve barely scratched the surface.
At the center, there’s a statue honoring the Heath Hen, a quiet reminder of the island’s history. The forest is still full of life today, with rare plants and wildlife throughout, making it one of the most important natural areas on the island. Luie Boone respects Heath the Hen… and will be on his absolute best behavior here.
Tisbury Great Pond
Tisbury Great Pond sits within Sepiessa Point Reservation, and Luie Boone immediately clocks this as a top-tier water spot. Formed by glacial melt long ago, the pond stretches out with calm, open views.
There’s a long stretch of protected shoreline, much of it visible from the trails and a sandy beach at the southern end that’s perfect for a walk.
Luie Boone would like to remind everyone to watch for oyster shells because those are not friendly on paws.
It’s a great place for swimming, paddling, or just hanging out by the water, with both sunrise and sunset views that make it worth the trip. Dogs can join for a walk or a quick dip, which Luie Boone fully supports. Access takes a little effort since you’ll need a canoe or kayak from nearby preserves, but that just makes it feel more like an adventure. During shorebird nesting season, there may be restrictions, and Luie Boone will be respecting the birds… while still thinking about them.
Wasque
Wasque, pronounced “way-skwee,” is one of those places that’s always changing, shaped by storms, currents, and shifting sand. Luie Boone hears “ever-changing coastline” and is both excited and slightly on alert.
Located on Chappaquiddick, it’s only accessible by foot or boat, which makes it feel a little more remote and worth the effort. Once you’re there, you’ll find open space, coastal views, and trails through rare sand barrens where leashed dogs are welcome.
The landscape is beautiful but unpredictable, so it’s important to stay aware. Protected bird areas should be respected, and dunes are off-limits. Luie Boone understands… mostly. There are also seals in the area, which may attract sharks, so swimming isn’t always a great idea. This is one of those places where you take it all in, move carefully, and appreciate the wild side of the island.
Among the Flowers
Located within walking distance of Edgartown Harbor, Among the Flowers is a go-to spot for fresh, feel-good meals, and Luie Boone is already interested in the garden patio situation. It’s been family owned and serving locals and visitors for decades, which says a lot.
Dogs are welcome to join outside, where there’s water and treats waiting, which Luie Boone considers excellent hospitality. Breakfast and lunch are the focus, with plenty of options that make it easy to settle in and stay a while. It’s the kind of place you stop once and end up thinking about later. Luie Boone would recommend securing a patio seat and staying close to the snacks.
Luie Boone's Pet Peeve about
Martha's Vineyard, Massachusetts
There's just so much to love about this vacation destination, but there's one thing that's got Luie Boone's leash in a twist. He woofed:
It started when my hoomans used that serious planning voice and the suitcases came out. I heard “Martha’s Vineyard” and “beach,” and suddenly this felt very important. Beaches mean sand, sand means running, and running is my favorite thing in the entire world. Then they started talking about birds. Apparently, there are a lot of shorebirds. Like… a lot. Just standing on the sand, existing, waiting. My hoomans got that worried tone, the this might be a problem voice, which is confusing because this sounds like incredible news. They kept saying things like “constant temptation” and “he’ll have to stay on a leash.” I don’t think they understand that birds don’t follow rules. They run, they flap, they take off at the last second, and my legs just… go. That’s not a choice, that’s instinct. They want a calm beach vacation. I want to sprint across the sand while birds scatter dramatically into the sky. We may not be aligned on this. I will try to be good. I really will. But if a bird runs past me… I cannot make any promises.
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