Visiting Martha’s Vineyard? 9 Things to Do

You’ll find Martha’s Vineyard’s best experiences beyond expensive resorts. Marvel at the dramatic 130-foot Aquinnah Cliffs, bike the scenic 6-mile coastal path between Oak Bluffs and Edgartown, and wander through colorful Victorian gingerbread cottages. Take the $5 ferry to quiet Chappaquiddick’s East Beach, catch sunset at Menemsha Harbor, and explore Edgartown’s historic whaling mansions. Don’t miss America’s oldest carousel and hiking Menemsha Hills for panoramic views—plus one unexpected agricultural adventure awaits.

Marvel at Aquinnah Cliffs and Climb the Historic Lighthouse

When you arrive at Martha’s Vineyard’s western tip, the Aquinnah Cliffs will immediately grab your attention with their striking multicolored layers of red, orange, yellow, and white clay rising 100-130 feet above the Atlantic. These million-year-old glacial formations stretch one mile and hold fossils of whales and prehistoric creatures.

You’ll view the cliffs from Aquinnah Circle overlooks and viewing platforms—climbing the cliffs themselves is prohibited since they’re protected by the Aquinnah Wampanoag Tribe.

Head to nearby Moshup Beach for shoreline access with the cliffs as your backdrop.

Don’t miss climbing the historic Gay Head Lighthouse, which operates Memorial Day through Columbus Day. This red-brick beacon offers commanding views of the Elizabeth Islands, Buzzards Bay, and spectacular western sunsets. The lighthouse was famously featured in Steven Spielberg’s Jaws.

Bike the Oak Bluffs to Edgartown Coastal Path

Since biking is one of Martha’s Vineyard’s most popular activities, you’ll want to tackle the scenic 5-6 mile Oak Bluffs to Edgartown coastal path that showcases the island’s best shoreline views.

This paved, flat route follows Beach Road alongside Joseph Sylvia State Beach and Sengekontacket Pond, making it perfect for beginners and families.

You’ll pass the famous “Jaws Bridge” halfway through—a cultural landmark where summer visitors jump into the pond below.

The ride takes 35-40 minutes at a casual pace, with sweeping Atlantic views and excellent sunset photo opportunities. Check the current weather conditions before heading out to ensure optimal comfort and safety during your coastal ride.

Park for free along Beach Road’s north side, or rent bikes in either town.

Consider taking the shuttle back for a one-way trip, or extend your ride to South Beach for additional mileage.

Wander Through Oak Bluffs’ Colorful Gingerbread Cottages

After completing your coastal bike ride, you’ll discover one of Martha’s Vineyard‘s most enchanting neighborhoods just steps from Oak Bluffs’ downtown area. The gingerbread cottages within the Martha’s Vineyard Camp Meeting Association grounds offer a free walking tour through 300+ colorful Victorian homes.

These compact Carpenter Gothic structures feature elaborate scroll-cut trim and bright pastel paint schemes in pink, purple, turquoise, and yellow. Originally built as simple Methodist camp meeting shelters starting in the 1860s, they’ve evolved into a dense fairytale-like streetscape.

Walk the narrow paths around Wesleyan Grove‘s central iron tabernacle to see the best examples. Visit the Cottage Museum at the campground entrance for historical context. Many cottages display decorative name signs and welcoming front porches with rocking chairs. If you’re fortunate to visit during the annual Illumination Night, you’ll witness the magical sight of cottages decorated with glowing paper lanterns in a tradition that began in 1869.

Take the Ferry to Chappaquiddick Island’s Quiet East Beach

From Oak Bluffs’ charming Victorian streets, head southeast to Edgartown Harbor for one of Martha’s Vineyard’s most unique adventures. At 53 Dock Street, catch the On Time Ferry to Chappaquiddick—America’s oldest ferry business operating since 1807. The 90-second crossing costs about $5 for foot passengers or $15 with a car.

Once across, you’ll need AWD or an SUV for the sandy, unpaved roads leading to East Beach. This Atlantic-facing shoreline offers undeveloped coastline with strong surf and sweeping ocean views. You’ll find fewer crowds here, making it perfect for walking, surfcasting, and birdwatching. During the short voyage, enjoy panoramic views of the coastline and Katama Bay as you approach the island.

Expect minimal amenities, so bring water and snacks. Arrive early during summer—limited parking and the ferry’s small capacity create wait times during peak hours.

Catch Sunset at Menemsha Beach Harbor

While Chappaquiddick offers solitude, Menemsha Beach Harbor delivers Martha’s Vineyard’s most celebrated sunset experience. This west-facing Chilmark beach lets you watch the sun drop directly into Vineyard Sound, creating brilliant orange and pink skies that often draw spontaneous applause from crowds.

You’ll need to arrive 1-2 hours early since parking fills quickly during peak summer. The beach welcomes non-residents, making it accessible for all visitors. Bring portable chairs and blankets for comfort during the wait.

Enhance your sunset with fresh seafood from nearby Menemsha Fish Market or Larsen’s Fish Market. You can enjoy lobster rolls and chowder picnic-style on the sand. Chilmark’s BYOB policy allows you to bring wine to complement your beachside meal.

The working fishing harbor adds authentic New England charm, with boats and jetties creating perfect photo opportunities against the colorful evening sky.

Explore Edgartown’s Whaling Captain Mansions and Waterfront

Edgartown’s Main Street and North Water Street showcase one of New England’s most intact whaling-era residential districts, where you’ll find 110 preserved captains’ homes built between 1835-1845. These white Greek Revival and Federal-style mansions feature distinctive “widow’s walks” on their rooftops, originally used for fire control and watching for returning ships.

Start at the Old Whaling Church (1843) on Main Street, then walk the tree-lined streets to spot notable homes like the Fisher-Bliss House and Captain Morse House. Don’t miss Dr. Daniel Fisher House at Main Street’s top. Among the architectural gems is the Captain Fisher House, built by Captain Charles W. Fisher who caught the largest sperm whale on record in 1884.

The Edgartown Lighthouse marks the harbor entrance where whaling ships once docked. You can explore this historic district on foot for free, making it perfect for budget-conscious travelers interested in maritime history.

Ride America’s Oldest Operating Carousel in Oak Bluffs

After exploring Edgartown’s maritime history, you’ll discover another piece of America’s past at Oak Bluffs’ Flying Horses Carousel—the nation’s oldest continuously operating carousel since 1876. Located at 15-33 Oak Bluffs Avenue, this National Historic Landmark features hand-carved wooden horses with real horsehair manes and glass eyes containing tiny lead figures.

Don’t expect typical carousel horses that move up and down—these remain stationary, making the “Flying Horses” name misleading. The rustic barn-like building houses alternating horses and chariots with restored nautical panels. The carousel sits on a triangular parcel bounded by multiple avenues and measures about 36 feet in diameter.

You’ll enjoy the traditional brass ring game while an automatic organ provides soundtrack.

The Vineyard Preservation Trust saved this rare Dare carousel from dismantling in 1986, ensuring future generations can experience authentic 19th-century amusement.

Hike Menemsha Hills for Panoramic Island Views

From Oak Bluffs’ nostalgic charm, head west to Chilmark for Martha’s Vineyard’s best hiking at Menemsha Hills Reservation. This 211-acre preserve offers three miles of interconnected trails without entrance fees, making it perfect for budget travelers.

You’ll tackle moderate terrain with rolling hills and rocky sections leading to Prospect Hill’s 308-foot summit—the island’s second-highest point. The payoff? Sweeping panoramic views over Vineyard Sound, Elizabeth Islands, and Aquinnah’s dramatic cliffs.

Plan 1.5 hours for the main loops, including the wooden viewing platform on Nashawakemuck Trail with its 180-degree coastal vistas. For a unique historical detour, explore the Brickyard Trail where remnants of an 1860s water-powered brickyard once produced 800,000 bricks annually for Boston and New York. The reservation’s open sunrise to sunset year-round.

Parking accommodates 16-20 cars off North Road. Wear sturdy footwear for roots and loose rocks.

Visit Island Alpaca Farm for a Unique Off-Beach Experience

When you need a break from Martha’s Vineyard’s beaches, Island Alpaca Farm at 1 Head of the Pond Road offers an unexpected agricultural adventure just two miles from Vineyard Haven ferry terminal.

You’ll spend 1-1.5 hours walking through pastures, observing alpacas in their natural-colored fleeces from white to black, and learning about fiber production through on-site videos.

The farm operates year-round, 10am-4pm daily, with general admission around $8 per person. The farm hosts around 30 alpacas, each with their own unique name and personality.

You can reach it via island public bus, making it accessible without a car.

Don’t miss the Discovery programs (typically 10-11am) for hands-on learning, and browse the farm store for alpaca sweaters, socks, and yarn.

Note that dogs aren’t permitted due to the animals’ sensitivity.

The Sum Up

You’ve got plenty to explore on Martha’s Vineyard without breaking the bank. Pack a bike, comfortable walking shoes, and a camera to maximize these free and low-cost activities. Don’t forget sunscreen for beach days and layers for evening harbor visits. Most attractions are accessible by bike or foot, saving you rental car costs. Plan your trip around the ferry schedule to Chappaquiddick, and you’ll experience the island’s best without overspending.