Aquinnah Cliffs, photo by Marnely Murray

Spending 24 hours Up-Island on Martha’s Vineyard is the perfect way to slow down and experience one of the most scenic and soulful parts of the Island. Known for its rolling farmland, dramatic ocean views, historic fishing villages, and vibrant arts community, the Up-Island towns of West Tisbury, Chilmark, and Aquinnah offer a serene escape from the busier Down-Island areas.

Whether you’re looking for coastal walking trails, farm fresh food, local art, or unforgettable sunsets, this guide will help you make the most of a full day Up-Island.

Morning in West Tisbury: Farms, Food, and Quiet Trails

Start your Up-Island adventure in West Tisbury, a pastoral town shaped by its agricultural heritage and tranquil natural landscapes.

photo by Marnely Murray

Breakfast at 7a Foods

Begin your day at 7a Foods, a West Tisbury staple loved for its excellent coffee, breakfast sandwiches, and fresh pastries. Whether you’re grabbing something warm from the oven or enjoying a hearty sandwich, it’s an ideal place to fuel up for a full day of exploring.

Browse Alley’s General Store

Just next to it is Alley’s General Store, the oldest operating retailer on Martha’s Vineyard. Browse books, snacks, toys, and Island essentials while soaking in the authentic local spirit.

North Tisbury Farmstand

A short drive up State Road brings you to the North Tisbury Farmstand, a bright and charming spot known for its fresh produce, baked goods, grab and go snacks, and local treats. It’s great for stocking up on fruit or picnic supplies for later in the day.

Polly Hill Arboritum, photo by Marnely Murray

Explore Polly Hill Arboretum

Just down the road sits Polly Hill Arboretum, a horticultural gem with rare trees, flowering shrubs, peaceful meadows, and easy walking paths. Whether you’re interested in botany or simply want a quiet natural space to explore, Polly Hill is a beautiful complement to your morning.

Walk the Trails at Cedar Tree Neck Sanctuary

Continue to Cedar Tree Neck Sanctuary, a conservation property offering shady woodlands, open meadows, and a serene stretch of shoreline. It’s one of the most scenic and restorative trails on the Island and a perfect way to begin your Up-Island immersion.

Late Morning: West Tisbury Arts and Island Landscape

Up-Island has long attracted artists and creatives who draw inspiration from its natural beauty.

The Granary Gallery

The Granary Gallery at the Red Barn is one of the Island’s premier art destinations, showcasing painting, photography, sculpture, and mixed media from local and nationally recognized artists.

The Field Gallery, photo by Marnely Murray

The Field Gallery

Nearby, the Field Gallery offers bright, contemporary art and whimsical outdoor sculptures that sway gently in the breeze. Wander the grounds before heading deeper Up-Island.

Lunch in Chilmark: Farmstands, Local Flavor, and Classic Island Stops

By midday, make your way to Chilmark, known for its rolling hills, scenic views, and strong agricultural roots.

Chilmark General Store 

A Chilmark classic, the Chilmark General Store offers sandwiches, salads, pizza, and prepared foods. Grab lunch and enjoy it on the porch, a beloved gathering spot for locals and visitors alike.

Beetlebung Farm Market

For hyper-local produce, Island-made provisions, and small batch goods, stop by the Beetlebung Farm Market. Their seasonal offerings reflect the best of Up-Island agriculture.

North Tabor Farm

One of the Island’s most charming small farms, North Tabor Farm is known for its organic greens, herbs, berries, and seasonal produce. Their farmstand is a must-visit for food lovers.

Orange Peel Bakery

On State Road, the Orange Peel Bakery features delicious baked goods, often made in their outdoor wood-fired oven. Whether it's bread, cookies, or seasonal treats, it’s the perfect stop for something sweet or savory before an afternoon of adventure.

Early Afternoon: Iconic Trails and Scenic Landscapes

Up-Island is home to some of the most breathtaking walking trails on Martha’s Vineyard.

Menemsha Hills Reservation

Explore Menemsha Hills, a stunning conservation area with forested trails, high overlooks, and sweeping coastal views. The vista from Prospect Hill is especially memorable.

The Brickyard Trail

From Menemsha Hills, continue onto The Brickyard Trail, which leads through wooded paths to the ruins of a historic nineteenth century brickworks. With its striking chimney remains and dramatic coastal scenery, it’s a fascinating off-the-beaten-path destination.

Menemsha Boardwalk, photo by Marnely Murray

Mid-Afternoon in Menemsha: A Historic Fishing Village

Next, make your way to Menemsha, one of Martha’s Vineyard’s most picturesque and historic spots.

Stroll the Docks

Menemsha’s working fishing harbor offers postcard-worthy views, family-owned shops, and a glimpse into the Island’s maritime heritage. Watch the fishing boats unload their catch or wander the quiet docks.

Photo by Marnely Murray

Grab a Lobster Roll from Menemsha Fish Market or Larsen’s Fish Market

Two Island favorites, Menemsha Fish Market and Larsen’s Fish Market, serve some of the freshest seafood on Martha’s Vineyard. Their lobster rolls are especially popular, making either spot a fantastic stop for an authentic Up-Island seafood experience.

Relax on Menemsha Beach

Enjoy your lobster roll on Menemsha Beach, where calm waters and views of Vineyard Sound make it one of the most peaceful places to unwind before heading to Aquinnah.

Late Afternoon in Aquinnah: The Gay Head Cliffs and Cultural Landmarks

A visit to Aquinnah is essential when exploring Up-Island.

The Gay Head Cliffs

The legendary Gay Head Cliffs are some of the most stunning coastal formations in the Northeast. Their layered clay colors shift with the sunlight, creating a dramatic and unforgettable view over the Atlantic Ocean.

Aquinnah Cultural Center

Located near the cliffs, the Aquinnah Cultural Center offers important insight into the traditions, history, and artistry of the Wampanoag Tribe of Aquinnah. It’s a meaningful stop for those interested in Island heritage.

Moshup Beach

If time allows, walk down to Moshup Beach, a wide, sandy shoreline with sweeping ocean views and the cliffs rising behind you. It’s one of the Island’s most breathtaking natural settings.

Evening: Dinner and Sunset on Menemsha Beach

After exploring Aquinnah, return to Menemsha for an iconic Up-Island sunset.

Pick Up Dinner from Larsen’s or Menemsha Fish Market

Both markets serve steamed lobster, chowder, scallops, shrimp, and more. Grab your dinner to go and bring it right down to the beach.

Sunset at Menemsha Beach

Widely considered one of the best sunset spots in New England, Menemsha Beach draws locals and visitors each evening as the sun sinks into Vineyard Sound. The combination of fresh seafood, gentle waves, and glowing skies is the perfect way to end your Up-Island day.

Dinner Option: Chilmark Tavern

If you prefer a sit-down meal, the Chilmark Tavern is an excellent seasonal option offering thoughtful dishes and a casual, welcoming atmosphere. It is a great choice for those looking for a more traditional dinner setting.

Why a Day Up-Island Is Worth It

Spending 24 hours Up-Island offers a deeper appreciation of Martha’s Vineyard’s natural beauty, agricultural roots, and quiet charm. From farmstands and art galleries to dramatic cliffs and fishing harbors, the Up-Island towns of West Tisbury, Chilmark, and Aquinnah provide a peaceful and inspiring escape.

Whether you're seeking hiking trails, fresh seafood, scenic vistas, or moments of quiet reflection, Up-Island delivers an unforgettable Island experience.

Note: Some of the spots mentioned are seasonal businesses; please check their websites for the most up-to-date information and hours.