Edgartown is what you're picturing when you think Martha's Vineyard -- highly suggest taking a walk down Main Street, do some shopping and grab an ice cream cone! There are a few boat charter tours out of Edgartown that'll give you a view from the harbor (need to be booked in advance) or just check out the harbor by land by walking out to the Edgartown Harbor Lighthouse. If you're renting a bike, it's worth a ride down through Katama (a residential, beachy section of Edgartown) to South Beach -- one of the major public beaches on-island. Can stop at the Katama General store on your way for a sammy or a snack. Or Morning Glory -- an on-island farm and super cute market that has some outdoor picnic tables if you want to take a biking break with an iced coffee and a muffin. Tours by biplane are available at the Katama Air Field -- or if you just want to watch the planes from the ground, there's a good spot for breakfast or a beverage "Katama Kitchen".
Favorite dinner spots include Atria (favorite), Alchemy and Behind the Bookstore (reservations required). If you don't have a dinner res, The Atlantic is first come first serve! Up main street there is the island brewery, Bad Martha's which serves half-decent pizza, too, if you want to stop in for a beer.
Oak Bluffs is 1 of 2 ferry ports on MV. You may be arriving in Oak Bluffs if you're taking the ferry over (if not, you're in Vineyard Haven!) The Tabernacle in Oak Bluffs is at the center of Cottage City -- a big grouping of historical "gingerbread" style summer homes -- worth a walk around with a coffee or a cocktail (and is right next to where the Welcome Party will be!)
Chowder House (by ferry)
#1 Rec is to check out The Grey Barn and Farm -- a local dairy and cheese farm. They have a farmstand on the property that sells their cheese as well as ridiculously tasty baked goods (as long as you get there first thing in the AM -- they sell out fast!) and sometimes even has a coffee cart parked next to their picnic tables. Grey Barn offers tours of their cheese caves, too, if you're interested in the process! Next door to Grey Barn is The Yoga Barn, if you need to work off those recently acquired calories. Menemsha is a section of Chilmark that's worth a visit -- old school fishing village where you can walk down the dock or sit on the beach. Best lobster roll on island.
#1 Lobster Roll at Menemsha Fish Market -- fair warning, there is only outdoor seating so make sure it's a decent day before you show up. Chilmark Tavern -- BYOB dinner spot; reservations required.
Check out the Aquinnah Lighthouse, Clay Cliffs and walk down to the beach. Great area for biking, too -- there is a "bike ferry" that runs from Menemsha to Aquinnah some days of the season if you want to make a day of it.
If you want to blow it up -- Outermost Inn (reservations required). Set menu with a view; sunset that'll change your life
West Tisbury is the artsy/farmy part of the island. If you're a sucker for a New England stone wall... worth a drive down Middle Road. West Tisbury Farmers Market is open Wednesday and Saturday AM. Stop for a lassi or some fresh produce at Mermaid Farm. Granary Gallery if you're in the market for some island art!
Black Sheep and MV Fish House are right by the Airport if you're landing and need a grab and go lunch! 7A Foods has sammies, closer to the main strip of West Tis. State Road has great vibes, good to brunch. And pop next door to Martha's Vineyard Glassworks!
Vineyard Haven is 1 of 2 ferry ports on MV. You may be arriving in Vineyard Haven if you're taking the ferry over (if not, you're in Oak Bluffs!) Martha's Vineyard Museum -- beautiful cultural and art museum that's worth a look! Main street in Vineyard Haven is pretty cute and has some solid shopping!
Little House Café is our favorite spot for lunch on-island. Must order: Strawberry Shortcake. Looking for grab and go after you land? Waterside Market for sammies. Formal dinner with reservations: Garde East and Beach Road (both come with a view!)
Chappy is a couple-minute ferry ride from Edgartown -- worth checking out for a few hours if you've got the time! Mytoi Gardens- serene secluded beautiful Japanese style gardens and you can follow up by checking out The Dike Bridge another minute drive away (which now has guardrails- no guardrails in 1969 when Teddy drove over it) NO FOOD or really anything else on Chappy. Don't get stuck.
South Beach (where Beach Day will be) State Beach Norton Point (drive on, need a permit); but can walk along out to Lucy Vincent (typically private, but Friday 9/16 is first "off season day"
All hikes can be located on: Sheriff’s Meadow Foundation website or Trustees of the Reservation. Our favorites include: Menemsha Hills -- Walk through the woods to the water, and definitely take the path that leads you past The Brickyard (remains of an old brick factory on a rocky beach) Sepiessa Point Reservation -- walk along Great Pond in West Tisbury; sometimes you'll even see an otter!
There are plenty of biking trails on the island! And many spots to rent bikes, but the one we frequent is Edgartown Bicycles. Favorite spots on the island to bike include: Around Menemsha In Aquinnah/Lobsterville (hilly) Chappaquiddick (take ferry across, ride over to the beach/bridge)