Seven Things to Eat, Drink, and Do This Labor Day Weekend in Boston

Hit a sunny new rooftop patio, bring a restaurant-packed picnic to a park, or celebrate the return of a legendary Boston hot dog.

It’s a long weekend, Boston! Make the most of it by getting outside, enjoying the sunshine, and helping yourself to some merry moments—whether you’re enjoying a fruity cocktail at a breezy new rooftop patio, bringing a restaurant-packed picnic to the park, or indulging in the return of an iconic Boston hot dog. Here are seven delicious ideas.

Photo courtesy of Rosebud

Have a lunchtime fish fry at Rosebud American Kitchen & Bar

No need to battle Cape Cod traffic if you want to work in one more late-summer run to a classic roadside seafood shanty—just head to Somerville’s Davis Square. That’s where you’ll find Rosebud, housed inside a historic dining car, which recently launched a Friday lunchtime menu dubbed the “Jaunty Jack Fish Shack”; it’s named for the lobster roll-doling eatery that once occupied the site. From 11 a.m.-3 p.m., Rosebud is serving fish shack specials like a fried soft-shell crab BLT, beer-battered haddock sandwich, extremely on-trend Rhode Island-style calamari, and more. Although “Jaunty Jack” is a weekly Friday special, Rosebud is also adding a special Labor Day installment for Monday, September 7.

381 Summer St., Somerville, 617-629-9500,

Courtesy of Terra

Sip a cocktail on Terra’s new sun-splashed rooftop patio

Tons of amazing new patios have popped up around Boston over the last few months as restaurants hustle to maximize their outdoor space. Here’s the latest: the third-floor terrace at Terra in the Back Bay. Expanding on the garden-like aesthetic of the main dining room, the al fresco space is filled with lush greenery, terracotta planters, and twinkling string lights—under them, you’ll be sipping summer cocktails like the herbaceous Italian Greyhound of Punt e Mes vermouth and grapefruit. And the food? That comes courtesy of chef Dan Bazzinotti, whose tremendous work over Terra’s huge open-flame grill turns out spiedini skewers of Gulf shrimp with Calabrian chili, 7-bone steaks and whole fish, and much more.

Inside Eataly at the Prudential Tower, 800 Boylston St., Boston, 617-807-7307,

Affogato kits at Oddfellows. / Photo courtesy of OddFellows Ice Cream Co.

Take home an affogato kit from OddFellows Ice Cream Co.

Fact: Bostonians love iced coffee. Boozy coffee-covered ice cream, then, shouldn’t be too hard a sell around here—and indeed, that’s exactly what’s landed at OddFellows (in take-home-friendly form, no less). The Chestnut Hill location is the only outpost of the small, NYC-based scoop-shop chain to be pairing pints of ice cream with eight-ounce bottles of Mr. Black, a cold brew coffee liqueur. So pick up your $29 kit and pour a generous pool of the caramel- and cacao-flavored stuff over each scoop; it’ll put a little extra pep into the last leg of summer.

55 Boylston St., Chestnut Hill, 617-505-6446,

Roman-style pizza at Mr. Roni Cups. / Photo courtesy of Mr. Roni Cups

Try Roman-style pizza at the just-opened Mr. Roni Cups

While you’re picking up your OddFellows affogato, check out its new neighbor at the Street, an open-air retail neighborhood in Chestnut Hill: Mr. Roni Cups, a playful concept specializing in Roman-style pizza, rotisserie chicken and sushi tacos, it’s the latest from chef Tim and Nancy Cushman, the restaurateurs behind Boston’s legendary O Ya. The Cushmans were about to open Bianca, a family-friendly space anchored by a wood-fired oven, when COVID came down in March. To hold us over until the full Bianca menu gets up and running, they’ve started operating Mr. Roni Cups there—offering indoor and outdoor dining, as well as takeout and delivery. The early highlight is the Roman-style pies, available in traditional square slices and by the half or full pan; toppings range from roasted garlic bechamel to shaved black truffle and, of course, pepperoni. But you’ll also find half- and whole-bird chicken plates with Peruvian BBQ sauce, kicky cocktails, and nori-wrapped tacos of spicy raw fish that recall the funky sushi at sibling spot Hojoko.

47 Boylston St., Chestnut Hill, 857-576-8300,

Picnic kit. / Courtesy of Cafe Landwer

Plan a picnic with help from Cafe Landwer, GreCo, or Piattini

Soak up these still-warm September weekends by finding a grassy plot for a picnic-style feast—ideally, one that’s already been assembled for you. Israeli cuisine outfit Cafe Landwer is currently offering three different themed picnic options: anchored by shakshouka, burgers, or vegan stir fry, each $60 assemblage includes sides like halloumi sticks with marinara sauce or family-style hummus bowls, feeds four people, and comes packaged in a reusable jute bag. (You can also add a $50 mimosa kit, which pairs a bottle of Prosecco with a selection of juices.) Through Monday, September 7, you can also pick up a GreCo picnic box from the Seaport location of the Greek fast-casual favorite; each $94 assortment feeds up to four people with pork and chicken gyros, loukaniko sausage, salad, spicy feta and tzatziki dips, deep-fried doughnut holes, a bottle of natural Greek red wine, and more. (They even toss in a picnic blanket, sunscreen, and deck of cards.) Finally, the Back Bay’s Piattini restaurant just launched to-go boxes of assorted cheese, including the Summer Picnic ($89): five selections of fromage accompanied by fig spread, quince paste, and more.

Cafe Landwer, 900 Beacon Street, Boston, 857-753-4035; 383 Chestnut Hill Ave, Boston, 617-383-5786,
GreCo, 200 Pier 4 Blvd., Boston, 617-572-3300,
Piattini, 226 Newbury St., Boston, 617-536-2020,

The Boston Speed Dog has arrived to Troquet on South. / Photo courtesy Troquet on South

Enjoy the return of the famous Boston Speed Dog at Troquet on South

Between backyard cookouts and baseball season, late-summer is prime time for hot dogs—which is why we’ve collected some of our all-time favorites here. But now you can add the refined downtown restaurant Troquet on South to the list of spots on your hot dog crawl, because chef-sommelier Chris Campbell has revived the original recipe for the Boston Speed Dog—which hasn’t been seen since 2013. That’s when the 1975-founded hot dog wagon that first dispensed these dogs took itself off the road; Campbell, a friend of founder Ezra “Speed” Anderson, has brought back the half-pound all-beef frank—topped with chili sauce, sweet relish, mustard, and onion—for a whole new generation of dog lovers. It’s available for takeout, delivery, and during lunch and dinner service.

107 South St., Boston, 617-695-9463, and

September flavors at Kane’s Donuts. / Photo courtesy of Kane’s Donuts

Get a taste of a classic county fair at Kane’s Donuts

Sadly, this fall season won’t allow for crowded fairground midways packed with people, as well as every type of deep-fried concession under the sun. (Although if you head to Topsfield, you can certainly enjoy some snacks in your car at the fairground’s new drive-in movie theater.) So shout-out to Kane’s, one of Boston’s best donut makers, for introducing special flavors for September that cull inspiration from autumn carnivals: the caramel apple candy crunch donut, topped with dulce de leche; the cake-style cinnamon apple cider donut; a pumpkin cheesecake donut, studded with toasted pepitas; and the “fried dough(nut)” with salted sweet-cream butter and a dusting of cinnamon-sugar. Available all month long, they’ll have to hold us over until our next spin on the ferris wheel.

Two International Place at 90 Oliver St., Boston, 857-317-2654; 1575 Broadway (Rt. 1), Saugus, 781-558-5179; 120 Lincoln Ave., Saugus, 781-233-8499,