Best Dining Deals & Restaurant Specials On Martha’s Vineyard: The Frugal Foodie On The Town In Edgartown

This might sound crazy, but I think the best town to grab a bite to eat and make the most of your money this time of year is Edgartown. There’s something fun and frugal happening almost everyday of the week.

This is our third Frugal Foodie Guide, and we’re hitting the town, to see what the restaurants in Edgartown have to offer, and believe me there’s a lot.

Square Rigger

The Square Rigger Edgartown Restaurant Frugal Foodie Dining DealThe Square Rigger is celebrating the year-round clientele with two to three $20 dinner options each week. These meals are hearty and perfect for the end of winter.

You can try the homemade Cottage Pie which has tender morsels of beef in a rich gravy, baked with vegetables and topped with mashed potatoes and a sprinkling of cheese. Sounds good! You can add a salad to the meal for an additional $4.50.

Square Rigger Lobster Roll Frugal Foodie Dining Deal EdgartownMaybe that’s a little heavy? Perhaps the Square Rigger’s Lobster Roll is a good option. You can have it chilled with mayo or served warm sauteed with melted butter, and a cup of chowder.

One more tease for all you Square Rigger fans, the Chicken Marsala is on this list of $20 options. This family recipe that’s been around for years is served on a bed of warm mashed potatoes. Hungry yet?

If so, you’ll have to wait until the weekend. The Square Rigger is open Thursday thru Sunday during the off-season.

Here’s a little history for you about the Square Rigger’s building: Built about 1800 by Capt. Thomas Marshall Pease, who was a whaling captain and sailed square-rigged ships, the old house communicates a feeling of the Island in days long gone by.

Now, I understand the name and appreciate it, and the restaurant a lot more. This is the year I finally try the Rigger.

Henry’s Bar

Henry’s at the Harbor View Hotel is also offering some great opportunities to make dining out more affordable off-season. Wednesday nights are 2-for-1 small plates and entrees.

Thursday’s are Throwback Thursday with a TBT vintage food with a modern twist. It’s three-courses and  prix-fixe for $30. The menu changes weekly.

Also, on Fridays, oysters are $10 for a half dozen Honeysuckle Farm Oysters — a great deal for the Happy Hour crowd.

Edgartown Restaurant Henry's - Frugal Foodie Dining Deal Grilled OystersHenry’s 2-for-1 is not only an amazing deal, but it’s a culinary treat. I went last week, and let me tell you, the food was so good. I started with Grilled Honeysuckle Farm Oysters. I love grilled oysters and these were some of the best I’ve ever had.

Henry's Linguini & Clams with squid ink pasta Martha's Vineyard RestaurantsI then had the Linguini & Clams, which had housemade chorizo sausage and get this, came with squid ink pasta. The pasta was the color of squid ink, that rich blue, and the texture of the noodles was nice, sort of like Soba noodles.

The meal was finished with homespun salted caramel ice cream for me and the kiddos and my husband had housemade ice cream sandwiches with bacon. He was in absolute heaven

I like Henry’s. Cozy up in one of the banquettes and just sit back and relax. I always feel like I’m on a mini vacation when I’m there, and now with the great deal this winter, I need to be there more often.

The Grill On Main

The Grill on Main Martha's Vineyard Restaurants Dining Deals Frugal FoodieThe Grill on Main has some great dining deals for all you Frugal Foodies. First of all, entrees are 2-for-1 Thursday thru Saturday. How great is that! Those are the nights you usually want to go out to eat.

The Grill has a great selection of entrees. Seriously, you can get lamb, chicken, duck, pork, chicken, and of course seafood. There’s something for everyone.

I also love that you can get a Caesar salad at The Grill. Sometimes you crave a classic like that, and not everyone has it. There are lots of other great apps to choose from if you want something a little more interesting than salad.

Busy on the weekend and not able to make the 2-for-1? Well, The Grill on Main has a three-course Prixe Fixe menu for $36, as well as their dinner menu on Mondays, Tuesdays, and Wednesdays. So, you can pretty much go here any day but Sunday and have an affordable meal. Luckily on Sunday you have Atria


Burgers at Atria Frugal Foodie Dining Deal EdgartownAh the Brick Cellar Bar at Atria – one of my favorite places.  I know there’s so much more to this place restaurant than Taco Night (Wednesday) and Burger Night (Sunday) when selected items are 2 for 1, but I love going to Atria on these nights. The place is usually packed and it’s cozy and fun this time of year.

The food is always good and you bound to see a lot of people you know. Best to make a reservation.

Tacos at Atria Edgartown Restaurant Frugal Foodie Dining Deals Martha's VineyardI love these nights so much, I’ve written blogs on both of them, Where To Eat During The Off-Season On Martha’s Vineyard – Taco Wednesdays At Atria Of Course and Burger Night At The Brick Cellar — Good Food & Fun Sunday Nights In Edgartown. Both of these will give you an inside look at these two great nights out.

A Full Week of Deals

Let’s think about this. There is someplace you can get a deal seven nights a week on Martha’s Vineyard.

You can start with Burger Night at Atria, 2-for-1 Monday at Offshore, Prixe Fixe at The Grill on Main on Tuesday, Henry’s 2-for-1 on Wednesday, hit the Square Rigger on Thursday, the Black Dog’s lobster night on Friday, Prime Rib night at the Ocean View on Saturday, and start all over again, or mix it up depending on what you’re hungry for.

If you missed our Frugal Foodie Dining Deals in Vineyard Haven, or Oak Bluffs, what are you waiting for? Let me know if there’s a special you think I should mention in the Frugal Foodie. Email me at

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2 thoughts on “Best Dining Deals & Restaurant Specials On Martha’s Vineyard: The Frugal Foodie On The Town In Edgartown”

  1. A gaggle of gals that are still on island , at least until Jan. 1st ,have been getting together in Edgartown for Thursday night drinks and light food. Do you know which restaurants have happy hour drinks… help with our budgets!! We usually gather 5:30 -7:00 and discounted drinks would help. We did do BTB last night but would like to mix it up. Thanks for your help.

    1. Love that you did BTB! Sharky’s always has specials – but as far as where else…not quite sure yet. Since Happy Hour is not legal in MA a lot of restaurants don’t seem participate.

      However, Detente which is still open and has price apps from 5:30 – 6:30pm!!

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