Best Beach: Lucy Vincent Beach
South Road, Chilmark
Runner-up: Lambert’s Cove Beach
Lambert’s Cove Road, West Tisbury
Chilmark residents, renters, and their lucky guests flock to the picturesque swath of Lucy Vincent Beach with its ever-changing clay cliffs and pounding surf. Clothing is optional on one subtle stretch. Lambert’s Cove’s fine sand and mellow water is a vibe all of its own.
Best Bike Rental/ Shop: Wheel Happy
8 South Water Street, Edgartown, 508-627-5928, wheelhappybicycles.com
Runner-up: Edgartown Bicycles
212 Upper Main Street, Edgartown, 508-627-9008, edgartownbicycles.co
Whether you’re in the market for a brand new or durable second-hand bike, or a full day rental, Phil Hughes of Wheel Happy has the wheels and the knowledge to get you cruising. Edgartown Bicycles offers sales, service, and rentals.
Best Fishing Charter: Skipper/Vineyard Sound Charters
Oak Bluffs Harbor, Slip 74, Oak Bluffs, 508-693-1238, mvskipper.com
Runner-up: Coop’s Bait & Tackle Charters
147 Edgartown– West Tisbury Road, Edgartown, 508-627-3909, coopsbaitandtackle.com
Captain John Potter has been fishing Vineyard and Nantucket Sounds for more than forty years. He’ll make a seafaring fisherman out of just about anyone aboard his trusty boat Skipper. Coop’s Bait & Tackle Charters is known for its top-notch gear and know-how.
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/felixneck
Whether you’re a beach walker or woods walker, Cedar Tree Neck has the best of both. With 400 acres of vistas, flora, and fauna, this spectacular sanctuary is a favorite of outside enthusiasts. Felix Neck offers four miles of woodland, salt marsh, and shoreline trails.
Best Place to Kayak: Sengekontacket Pond
Runner-up: Edgartown Great Pond
Plenty of ponds are worthy of a paddle, so what sets Sengekontacket apart? Easy access, shoreside rentals, and diverse ecology for starters. Kayakers can explore salt marshes by day and paddle by moonlight in the evening. The shores of Edgartown Great Pond attract an array of beach nesting shorebirds.
Best Sailing Charter: The Black Dog Tall Ships
Vineyard Haven Harbor, 508-693-1699, theblackdogtallships.com
Runner-up: Catboat Charters
1 Dock Street, Edgartown, 508-524-6903, catboatcharters.com
The maritime adventure of your dreams awaits aboard the Black Dog’s two schooners, Shenandoah and Alabama. Whether that dream involves raising the sail or simply sitting back to feel the sun and wind on your face is entirely up to you. You’ll recognize Catboat Charter’s Tigress from Edgartown Harbor with her signature stars-and-stripes look.
Best Summer Camp: Camp Jabberwocky
200 Greenwood Avenue Extension, Vineyard Haven, 508-693-2339, campjabberwocky.org
Runner-up: The FARM Institute
14 Aero Avenue, Edgartown, 508-627-7007, thetrustees.org/tfi
For more than six decades, Camp Jabberwocky has been a hub of summertime fun and adventure for children and adults with disabilities. This summer, their mission of empowerment, adventure, and fun continues online. The FARM Institute connects kids ages four to seventeen with friendly farm animals and fresh harvests.
