Best Beach: Lambert’s Cove Beach

Lambert’s Cove Road, West Tisbury

Runner-up: State Beach

Beach Road, Edgartown and Oak Bluffs

Lambert’s Cove Beach is a favorite for West Tisbury locals and visitors, known for its calm waters, soft sand, and rolling dunes. Just remember, you’ll need a parking sticker in the summer to get in! State Beach offers miles of sandy shoreline, gentle waves, and that classic Vineyard vibe, interrupted only by the iconic Jaws Bridge.

Best Bike Rental/Shop: Edgartown Bicycles

212 Upper Main Street, Edgartown, 508-627-9008, edgartownbicycles.com

Runner-up: Wheel Happy

8 South Water Street, Edgartown, 508-627-5928, wheelhappybicycles.github.io

If you want to explore the Island on two wheels, Edgartown Bicycles has you covered with bikes for every trail, plenty of kid-friendly options, and helpful staff ready to share tips or make repairs. Wheel Happy is another great spot to buy or rent bikes and get rolling hassle-free.

Best Fishing Charter: Tomahawk Charters

Menemsha Harbor, 508-645-3201, tomahawkcharters.com

Runner-up: Skipper/Vineyard Sound Charters

Slip 74, Oak Bluffs Harbor, 508-693-1238, mvskipper.com

A trip aboard Tomahawk Charters all but guarantees a haul of striped bass, bluefish, or fluke. With Skipper/Vineyard Sound Charters, the thrill of landing a big catch makes for an unforgettable trip.

Best Nature Walk: Cedar Tree Neck Sanctuary

Obed Daggett Road off Indian Hill, West Tisbury, 508-693-5207, sheriffsmeadow.org

Runner-up: Felix Neck Wildlife Sanctuary

100 Felix Neck Drive, Edgartown, 508-627-4850, massaudubon.org

A perennial favorite, Cedar Tree Neck Sanctuary stretches across hundreds of acres, with trails that meander through the Island’s diverse and beautiful habitats. Over at Felix Neck Wildlife Sanctuary, explore salt marshes, shorelines, and woodlands, plus enjoy plenty of birdwatching and family-friendly activities.

Best Place to Kayak: Sengekontacket Pond

Runner-up: Lagoon Pond

A kayak ride on Sengekontacket provides a fun, social experience on brackish water during the day and a peaceful view of the sunset in the evening. Or bring your kayak to the Lagoon and paddle around Hines Point. Either way, wear a life jacket.

Best Sailing Charter: The Black Dog Tall Ships

20 Beach Street Extension, Vineyard Haven, 508-693-1699, theblackdogtallships.com

Runner-up: Catboat Charters

1 Dock Street, Edgartown, 508-524-6903, catboatcharters.com

Whether you’re looking to take in a sunset or a summertime fireworks show, a trip aboard the Black Dog Tall Ships’s schooner, Alabama, is a timeless way to experience the Island. Catboat Charters’s American Flag sail is a sight to behold in Edgartown Harbor.

Best Summer Camp: Camp Jabberwocky

200 Greenwood Avenue, Vineyard Haven, 508-693-2339, campjabberwocky.org

Runner-up: The FARM Institute

14 Aero Avenue, Edgartown, 508-627-7007, thetrustees.org/tfi

It’s all about joy at Camp Jabberwocky, which for decades has been providing summer care and fun for children and adults with a wide range of disabilities. Kids can connect with the soil and learn about agriculture at the FARM Institute, a camp for future farmers and outdoor lovers. 

Best Tour Company: The African-American Heritage Trail of Martha’s Vineyard

508-693-4361, mvafricanamericanheritagetrail.org

(TIE) Runners-up: Felix Neck Wildlife Sanctuary

100 Felix Neck Drive, Edgartown, 508-627-4850, massaudubon.org

Vineyard Preservation Trust

58 North Water Street, Edgartown, 508-627-4440,
vineyardtrust.org

The African-American Heritage Trail of Martha’s Vineyard brings the Island’s rich Black history to life with more than forty plaques marking important sites. For nature enthusiasts, Felix Neck staff can take you on a guided kayak tour of Sengekontacket Pond. For even more Island history, book one of the walking tours led by the Vineyard Preservation Trust.