Dining Out: Chesca's

Over Labor Day weekend I fell in love with Martha's Vineyard. While I was enchanted by so many different spots, it was Edgartown that truly captured my heart. 

Edgartown, on the eastern side of the island, is a magical hybrid of the classic New England feel of Beacon Hill, mixed with the waterfront beauty and serenity of Provincetown. The red brick sidewalks line rows of houses worthy of Architectural Digest. Old fashioned lamp posts cast a warm glow of the town as the sun sets, making it as stunning during the evening as it is during the day. 

On our third night on the island we had a reservation at Chesca's on North Water Street, the main drag of Edgartown. We were a little bit early, so we decided to stop at L'etoile at the Sydney Hotel for cocktails. This popular bar is known for its martinis, so go ahead and indulge. I ordered an Aperol Spritz, a well-balanced cocktail (not too boozy, not to sweet) that was the perfect pre-dinner libation. 

At 7:30pm we strolled over to Chesca's. The restaurant has a large front porch with white rocking chairs. Those seats are highly coveted while couples and families wait for their tables. 

Chesca's Edgartown

There were six of us for dinner and the host walked us to a table in the dead center of the dining room. Next to us was a rowdy party of twelve. They were several drinks in, sporting matching sun glasses and snapping photos like crazy (with flash!). I felt like such an old lady, but the noise level resulting from our proximity to them was making it tough for me to enjoy myself. 

We ordered drinks while looking over the menu. Two our of friends had made a trip to Italy a few summers ago and they've become really knowledgeable about wine. They ordered a bottle of Caparzo, from a vineyard they had visited on their trip. 

Chesca's Edgartown

Two of the girls ordered blood orange martinis, a suggestion from our waitress. After a few sips, one described, "This is a slow sipping cocktail. It's pretty boozy and very tart, but I will happily nurse it throughout the meal."

Chesca's Edgartown

Once our food orders had been placed, we enjoyed baskets of warm focaccia bread with a side of white bean dip. 

Chesca's Edgartown

Since we were celebrating being on vacation all together, we decided to really go for it and order everything on the menu that sounded tasty. In the appetizer round, the first plate to arrive was bacon-wrapped and feta-stuffed dates. 

Chesca's Edgartown

They disappeared pretty quickly. One friend said, "These were phenomenal. The combination of the salty bacon and the sweet fig was sublime." Another friend chimed in, "This was perfectly balanced - the figs weren't too sweet, the bacon flavor wasn't too overwhelming and there was just the right amount of cheese."

At the far end of the table, a friend was nibbling on the bibb lettuce was Asian pears. He commented, "This dish is very light and refreshing. It has a great tang from the marinated onions and a touch of sweetness from the pears." 

Chesca's Edgartown

I couldn't resist the romaine lettuce with heirloom tomatoes, scallions and buttermilk dressing. Let's be honest, I ordered this for the dressing. 

Chesca's Edgartown

The girls were getting jealous of my buttermilk dressing and once I had eaten all the veggies, started using the focaccia bread to soak up the remaining drops.

Directly across from me, a friend was spooning bites of the Tuscan white bean soup (which is vegetarian). The night of this dinner was the one cold, rainy day of the holiday weekend, so soup was a smart choice to warm up quickly. 

Chesca's Edgartown

She described the soup as, "Piping hot, very flavorful and packed with fresh vegetables." 

As the appetizer plates were cleared, we were getting very excited for the main course. Unfortunately, it took another 35 minutes for our entrees to arrive (I blame it on that raucous table of twelve!). 

When the dinner did finally arrive, I was ecstatic to see such a generous portion for my order of the risotto primavera.

Chesca's Edgartown

The rice was mixed with snow peas, red pepper, mushrooms, tomatoes, corn and scallions. I loved the crunch of the pea pods and the pure, earthy flavor of the mushrooms. I would definitely order this again. 

Chesca's Edgartown

At the end of the table, a friend had ordered the sole picatta. The fish was sitting on top of sauteed spinach and was topped with artichoke hearts and a tomato and caper beurre blanc. I thought the flower garnish was a lovely touch.

Chesca's Edgartown

She took a bite and said, "This is so delicious. The fish is lightly battered and cooked expertly. The sauce was citrus-y and the spinach was a yummy accompaniment." 

Chesca's Edgartown

Across from her, her husband was cutting into his grilled, black angus, New York sirloin, served with roasted shallot Chianti butter, grilled asparagus and potato gratin. 

Chesca's Edgartown

When I asked how he was liking it, he replied, "The sirloin is rare, but has a nice crust on the outside. That shallot butter is very succulent. The asparagus has a nice sear, but is still crunchy. The potato gratin is to die for - so creamy, but with a crisped top." 

Chesca's Edgartown

Another friend opted for the pappardelle bolognese, which the menu described as veal ragu with pancetta, vidalia onions, tomato and cream. 

Chesca's Edgartown

After I took the first photo, she sprinkled on a bunch of parmesan cheese and insisted a take a few more shots. 

Chesca's EdgartownChesca's Edgartown

As she was twirling the pasta she mentioned, "I really wouldn't call this a bolognese. I expect that to be like a thick stew. This was more like red sauce with chunks of meat and veggies. But I give them bonus points for the house made pasta." 

Now, I have saved the best entree for last. Two friends at the table took advantage of Chesca's amazing (and if you ask me, genius) menu special called the bento box. Bento boxes are most commonly offered at Japanese restaurants and allow diners to sample many things on one tray, like soup, salad and an entree.

At Chesca's, they've adopted this approach and you can order a soup (clam chowder or Tuscan white bean), salad, mashed potatoes, sauteed veggies and a choice of protein (salmon, shrimp or chicken). This way, if you kind of want clam chowder, but you also want a salad and maybe you're also intrigued by a piece of fish, you can have every single one of those menu items. It's brilliant. 

Here are the two bento boxes that arrived to our table. Both friends selected the chicken marsala as their protein. 

Chesca's Edgartown

Though the concept is remarkable, I was so curious if the food would measure up. A friend shared, "The clam chowder is super creamy and not overly fishy. The salad is fresh and the mashed potatoes are rich, but not too heavy. The chicken marsala is very flavorful, but I wouldn't have minded a slightly bigger piece of chicken." 

All six of us thoroughly enjoyed our dinner (almost enough to forget how long it took to arrive). Though Chesca's has a dessert menu, we already had a post-dinner sweet tooth plan, so we asked for the check. The bill came with six pieces of chocolate. My kind of place! 

Chesca's Edgartown

After dinner we walked down North Water Street to Mad Martha's Ice Cream. We got two pints to take home - Bailey's Crunch and Reese's - which we planned to pair with the home made Nutella cookies we had back at the house. Calories don't count on vacation, right? 

If you're planning a trip to Martha's Vineyard, be sure to spend at least one afternoon or evening in Edgartown. Start at the Edgartown lighthouse. Get there for sunset and enjoy the stunning views as the sun goes down over the marina. Have a drink on the front porch of the Harbor View Hotel and then walk back toward the center of town for dinner. Be sure to save room for ice cream after your meal. The Bailey's Crunch at Mad Martha's is super decadent and worth every spoonful. 

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Molly Galler

Welcome to Pop.Bop.Shop. My name is Molly. I’m a foodie, fashionista, pop culture addict and serious travel junkie. I’m a lifelong Bostonian obsessed with frozen confections, outdoor patios, Mindy Kaling, reality television, awards shows, tropical vacations, snail mail and my birthday.

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38 N. Water Street
02539 Edgartown , MA
United States
Massachusetts US