Banners lobster roll
Photograph: Courtesy Banners Kitchen & Tap
Photograph: Courtesy Banners Kitchen & Tap

The best things to do for Labor Day in Boston

From the best brunches in Boston to the final North End Feast of the season, here's what to do over Labor Day weekend in the city.

Jacqueline Cain
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While getting out of town is great, there’s a lot to be said for staying in Boston for Labor Day Weekend. The weather is still awesome and there’s plenty to do, from hitting a local beach to checking out a hot restaurant. Schools are reopening and students are streaming into the city so it's buzzing with activity. Our on-the-ground editor picked the top events and activities to check out this Labor Day weekend in and around Boston—here's what's going on.

RECOMMENDED: Full guide to the 50 best things to do in Boston

What's going on at Time Out Market

Time Out Market in the Fenway has more than a dozen dining options and two bars, with fall flavors on the menu and a brand-new Italian kitchen. But showcasing the best of the city goes beyond just food and drink: The market hosts frequent events. This weekend, live DJs are on the decks Friday and Saturday nights, and Boston Event Guide returns on Saturday with the Boston Cocktail ChallengeNovember's Cocktail for a Cause continues, alongside new seasonal drinks, and Friendsgiving specials are hitting menus throughout the market.

Labor Day weekend events in Boston

When Mother Nature only allows a few months of true outdoor enjoyment, it’s important to maximize that time. Such is life in New England—and our restaurants rise to the occasion with plenty of al fresco dining options. While the tried and true best patios in Boston, rooftop spots and outdoor bars are always a good bet, the unofficial end of summer is high time to check out some of Boston's newer outdoor dining options.

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  • Things to do
  • City Life

It’s time for every undergrad—and let’s be honest, many apartment dwellers in the Greater Boston area—to celebrate a time-honored annual holiday, Allston ChristmasThis year, Stop & Shop is celebrating Allston Christmas in a fun way at its newest location. On Saturday, Aug. 31, and Sunday, Sept. 1, from 11am–1 pm both days, the local grocer is hosting an Allston Christmas party at its store at 305 Guest St. at Allston Yards. The store will have free food samples, holiday music playing—and even Santa Claus handing out goodies to shoppers, as well. Customers who spend $25 or more will receive a limited-edition Allston Christmas shopping bag. What better way to haul home your new-to-you toaster? The shopping bags are also available at the Mission Hill Stop & Shop.

Typically a weekend centerpiece, a three-day weekend is an opportunity for three days of brunch. And lucky for you: We just thoroughly overhauled our guide to the best brunch in Boston!  Whether you're looking to go big with caviar add-ons and Champagne trays, or just relax and have somebosy else fry your eggs for a change, there are options in every neighborhood. May we direct your attention to a few Monday brunch options: Trina's Starlite Lounge has a legendary brunch, and go-tos like Lincoln Tavern and Lone Start Taco Bar do brunch every day, including Labor Day. Two more ideas: Comfort Kitchen—our new No. 1 restaurant in Boston—is introducing brand-new Sunday brunch service at its Dorchester spot over the next couple weeks, including Sunday, Sept. 1. Also, Lone Star's suburban sibling, Deep Ellum, does Monday brunch every week, including this one. Head to Waltham to see what they're all about. 

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  • Eating

When the cookie’s powers combine with classic French technique? Well, delicious new traditions are born. PRB Boulangerie, with locations in Somerville, Cambridge, the South End and Time Out Market Boston, offers a totally Instagrammable "crookie" every weekend morning. The cookie-filled croissant has become a bit of a viral sensation and typically sells out by noon. With so many folks out of town for Labor Day weekend, it could be your chance to get your hands on one. 

  • Seaport District

The Seaport's "social darts" venue, Flight Club, is extending its weekend brunch menu to Monday, Sept. 1, so you can spend Labor Day with friends taking the game of darts to new heights. The various games Flight Club offers include dart racing, instant replay capabilities and more high-tech touches.

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As is tradition, admission to the Institute of Contemporary Art is free for Labor Day on Monday, Sept. 5. You can spend the day exploring all the galleries and exhibits, including the ICA Watershed in East Boston, which closes for the season after Labor Day. While the water shuttle between the museum and its annex is sold out for Labor Day weekend, the Watershed is also accessible via the Blue Line. (No ticket is ever required to visit the Watershed; remember that for next summer!)

  • Things to do
  • Allston/Brighton

A local marketplace centered on a beer garden-courtyard, the Charles River Speedway is always a one-stop shop in Brighton to check out a bunch of cool small businesses. But on Labor Day every year, the vendors team up to send off summer with a slew of specials, courtyard pop-ups and more fun. Check out this year's Labor Day Block Party on Monday, Sept. 2, between noon–5pm for live music, archery in Garage B, a pop-up outdoor cocktail bar by Birds of Paradise, a sake-spiked lemonade stand by The Koji Club and Rite Tea Bar, fun for kids like face-painting and more. Food and drink is pay as you go, but all events are free to the public.

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