Lis-t of my Favorite Spots on Martha’s Vineyard

My family is huge fans of the Vineyard, and I’m excited to simply share a list of our favorite places with you. Please comment any Frequently Asked Questions that I can add to my list!


  1. Places to Eat
    1. Best for Groups – RockFish 
    2. Best for Breakfast – Edgartown Diner 
    3. Best for Lunch (Take Out) – Rosewater
    4. Best for Lunch (Eat-in) – Behind the Bookstore 
    5. Best for Dinner – Lucky Hanks 
    6. Best for Drinks – Harborview Hotel 
  2. Instagrammable Spots
    1. Over by the Chappy Ferry, go to the top of the marina (up the stairs) – great view of the whole bay 
    2. Harbor View Hotel – walk out to the lighthouse 
  3. Things to Do 
    1. Chappaquiddick 
      1. Take a car out to Chappy and go for a hike

Oak Bluffs

  1. Places to Eat
    1. Best for Groups – Nomans 
    2. Best for Lunch – Lookout Tavern 
    3. Best for Dinner – Red Cat Kitchen 
    4. Best for Drinks – Cardboard Box 
  2. Instagrammable Spots
    1. Across from SummerCamp Hotel
    2. Fishing Pier 
    3. Gingerbread Houses 
    4. Ocean park 
  3. Things to Do 
    1. Walk around the Gingerbread Houses 
    2. Late Night Dancing – go to The Ritz for live music after 8 
    3. Donovan’s – get a Dirty Banana 

Vineyard Haven 

  1. Places to Eat
    1. Best for Groups – Black Dog Cafe 
    2. Best for Breakfast – Art Cliff Diner 
    3. Best for Lunch – Waterside Market 
    4. Best for Dinner – Net Result 
    5. Best for Drinks – Garde East 
  2. Instagrammable Spots
    1. In front of MV Museum 
    2. In front of Black Dog Cafe 
    3. Over by State Road/Net Result in Lagoon 
  3. Things to Do 
    1. MV Museum 

Up Island (Chilmark and Aquinnah) 

  1. Places to Eat
    1. Best for Breakfast – Scottish Bakehouse 
    2. Best for Lunch – Chilmark General Store 
    3. Best for Dinner – Larsen’s Fish Market 
    4. Best for Drinks – Outermost Inn 
  2. Instagrammable Spots
    1. Gay Head Lighthouse
    2. Menemsha Sunset 
  3. Things to Do 
    1. Watch the Sunset in Menemsha 

Our Favorite Places to Stay 

  1. Summercamp Hotel
  2. Clarion in Edgartown 

Frequently Asked Questions:

  1. What ferry do you take? My family mainly takes the Steamship Authority – you do not need to buy tickets in advance, there are free shuttles to the parking lots, and they have the most frequent service. Island Queen is fine as well, just runs less frequently.
  2. Where do you suggest staying? If there are more than 2 of you, I suggest an AirBnB close to a major town (Edgartown or Oak Bluffs). If there are 2, I suggest a hotel in either of those towns as well.
  3. Should I bring a car over? If you are staying outside of one of the bigger towns, it would be easiest if you did, though reservations in-season are required far in advance. If you are going in the off-season or for more than 3 days, you’ll definitely need one. The island is an hour long tip to tip, so Uber’s can get pricey if you want to travel between towns.
  4. How are the towns different? Oak Bluffs is younger, more family-friendly during the day with good night life at night. Edgartown is preppier and more classic New England. Vineyard Haven is a port town (sober), and Up Island towns are gorgeous yet rural. If I were going for a weekend I would suggest staying in Oak Bluffs as it is centralized.
  5. What is your favorite beach on island? I find parking more easily at State Beach (calmer waters), though if I’m there for the week I always try to make it out to South Beach at least once (more waves in the water, worse parking).
  6. What is the best time of year on the island? Shoulder Season! Between Memorial Day and July Fourth, or between Labor Day and Columbus Day. Warm enough to enjoy the beach and without the crowds.
  7. Can you camp on the island? Yes! Google it!
  8. What are your favorite picnic spots? Top 2 – on the pond by Net Result, out at Menemsha for Sunset
  9. What are the special events each time of the year? Will answer this later…too many!
  10. What’s Chappy like? Should I go? Take the 2 minute, 2 car ferry without a schedule, and head on over from Edgartown!  I love to take the car out and do a short hike (check TrailsMV app). There is only one small market on the island and it is very rural so don’t expect shops or much civilization. You can expect lots of natural beauty though!
  11. Can I expect traffic? In-season – yes! In OB and VH, near the ferry times expect some. In Edgartown, heading into town, expect it most times of day. Try a bike instead 🙂 Out of season- you’re good!
  12. What exactly is up island vs down island? Up Island is Chilmark and Aquinnah – its about a 30 minute drive from down island. Down Island is Edgartown, Vineyard Haven and Oak Bluffs – near the ferries. Those towns are between 10-20 minutes from each other.
  13. Should I do a group tour? If you’re on island without a car and only for a day/weekend – I think it’s the best way to go! Tour busses come out of OB and VH.
  14. Where’s the best nightlife? Edgartown or Oak Bluffs.
  15. What is open in the off-season? Great question! Very few places (less than 25%) are open year-round so just check individual websites just in case.
  16. What’s the distance in time between places? Vineyard Haven, Oak Bluffs and Edgartown are all about 10-20 minutes from each other. To get to Chilmark or Aquinnah expect to drive 25-45 minutes.
  17. What calendar do you use for events on the island? – MVacay is working on one of our own!
  18. What are the Martha’s Vineyard rites of passage? Jaws Bridge, Flying Horses, Gay Head Lighthouse, Back Door Donuts
  19. If you had the perfect day, what places would you hit up? Wake up for sunrise, go to Art Cliff for breakfast, walk around the gingerbread houses and pop over to State Beach and read in the morning. Head to Edgartown and have a drink on the porch of Harborview, walk around town and grab a quick lunch from Rosewater. Then, drive up to Menemsha around 6 to see the sunset. Go to Oak Bluffs and grab a drink from Cardboard Box and dinner from Red Cat. Watch some Live Music at the Ritz and head home 🙂

For more good recs, follow me at @mvacay or @elisabethmroche

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