It’s easy to think of Winthrop as the end of the world. The funny shaped peninsula juts out from Revere and hangs in the Atlantic Ocean east of East Boston. It’s cut off from the MBTA (the closest stop is Orient Heights after which your options are a Winthrop city bus or a two mile walk). This isolated beach town almost feels out of place, like it belongs on the New Hampshire seacoast or up in Maine. Only the din of airplanes flying low overhead landing at Logan Airport remind you just how close you are to Boston.

Being an idiot, I decide walking from Orient Heights to the beach in 90 degree heat is a great idea. My plan is to mosey along the coast and then circle around to the city center. I’ve got a healthy sweat going when I see Belle Isle Seafood to my right. The iconic restaurant and fish market stands tall, welcoming visitors to Winthrop’s city limits. I feel bad not stopping in for stuffed quahogs but honestly Anthony Bourdain already covered that and who am I to challenge the champ?

Once I reach the beach I realize there aren’t many places to eat along the water. You have to head inland one block to Shirley Street where there’s a small commercial district with a few restaurants. I stumble into Millie’s Kitchen. A sub shop where the menu boasts “Boaters: no matter where you are located, your order will be delivered to your boat via dinghy.” I immediately take a liking to this place. Millie’s is tiny, pumping out the usual sub shop fair at a high level using fresh, homemade ingredients. And by the volume of take-out orders I see while sitting there I can tell it has the community’s support.

Millie's lobster roll.
Millie's lobster roll gets it right.
Elisha Siegel

I order a lobster roll ($15.99) which comes out on a grilled and buttered hot dog bun overflowing with lobster meat that’s perfectly mayoed (that’s a word!) with crunchy bits of celery. It’s the perfect expression of the sandwich. Alongside is a chopped salad loaded with fresh vegetables. The care that goes into this food is undeniable. You can taste it.

Next, I head into the downtown area of Winthrop to eat at Blackstrap BBQ. Chef Chris Thompson, who — alongside business partner Kate Economides — opened Blackstrap in 2010, is an old friend. We go back to the early days of Highland Kitchen when we struggled to fill the place. Thompson hasn’t changed a bit. Ever the social butterfly, he seems to know everyone who walks into his restaurant, greeting them with a big smile and an inside joke.

Along with the sit-down component, Blackstrap’s catering business is the backbone of the company’s success and a big part of the reason Thompson and Economides are able to succeed in Winthrop. “In 2010 we opened our doors. It was just a small little hallway,” Thompson says. “A fifteen seat restaurant doing mostly takeout and delivery of really awesome barbecue. It was hard making a living off just selling meats. The catering was the anchor and the reason we were able to stay in business.”

A few years later, the two expanded their business and opened a bar. (There are plans to expand again.) But Thompson admits, small businesses in Winthrop aren’t exactly thriving. “We saw a community that was kind of struggling and needed some help. We thought we could breath a little life into the center. If we started this ball rolling other businesses would follow. We’re starting to see that.”

Wings at Blackstrap BBQ.
I came here to chew bubble gum and eat wings and I'm all out of bubble gum.
Elisha Siegel

I love Chris, but I’m here for the chicken wings ($6.99). Brined 24 hours with chilies and whole cumin seeds and then smoked, these wings alone are worth the trip. There are six sauce options but Thompson encourages me to go traditional with Buffalo. And just for fun, I throw in an order of North Carolina style pulled pork (tangy and spicy) with maple mashed potatoes, coleslaw and cornbread ($14.99).

It’s hard to argue that Winthrop looks depressed. Storefronts have been sitting empty for years and there are limited draws. But Thompson is hopeful things are changing. There is a local developer — who Thompson sees as an ally — working hard to rejuvenate Winthrop’s center. It’s a big job, but there is momentum at least when it comes to restaurants. Along with Blackstrap, La Siesta is serving up great Mexican food and the recent announcement that JW’s has been sold to Chef Jay Silva is welcome news.

Thompson hopes that a busy city center will make Winthrop more appealing to potential residents looking for homes outside Boston. “There are some really great things happening. Multiple times I’ve had young couples come in The Blackstrap and buy property in town just because we’re here. That makes me feel great — great about Winthrop.”

You can follow Elisha's musings on food, comedy and pro-wrestling @creamofsoup on Twitter and Instagram.

Blackstrap BBQ 47 Woodside Ave., Winthrop, 617-207-1783,
Millie’s Kitchen561 Shirley St., Winthrop, 617-846-0088
JW’s10 Putnam St., Winthrop, 617.207.3077,
La Siesta70 Woodside Ave., Winthrop, 617-846-2300,
Belle Isle Seafood1 Main St., Winthrop, 617-567-1619,