Boston shines year-round, but possibly more so in the fall when its universities and college campuses return to their normal bustling state, the Charles River is lined with rowers for the Head of the Charles Regatta and fall foliage sweeps across the Boston Common and the Public Garden. Whether you’re in town for a Red Sox or Bruins game, a show, or shopping, here’s what to see and where to eat and drink to make the most of an autumn weekend in Boston.
DAY ONE
Morning
For a classic, swanky stay in town, check in at the landmark Fairmont Copley Plaza, at the heart of historic and bustling Back Bay. Trendy boutique options include the hip The Verb Hotel in the Fenway, home to buzzy Japanese restaurant Hojoko, or the sleek Hotel Commonwealth at the heart of Kenmore Square. For edgier options, book an Airbnb in Somerville’s Davis Square or in Jamaica Plain—relaxed, young areas dense with bars and restaurants.
Then start with a sticky bun or house-made toaster tart from Flour Bakery + Cafe, which has locations in Fort Point, the South End, Back Bay and Central Square in Cambridge. Owner Joanne Chang is one of Boston’s beloved chefs: a Harvard grad, pastry whiz and 2016 James Beard award winner for Outstanding Baker.
Afternoon
In Copley Square, step into the central Boston Public Library, a magnificent building with a peaceful courtyard and an old-school reading room, plus free public art and architecture tours. Across the plaza, The Trinity Church, an iconic architectural landmark established in 1733, offers art and history tours. Nearby, the Prudential Center’s Skywalk Observatory is the only high-rise spot in the city that offers 360-degree views.
Hubway, Boston’s bike sharing program, has stations around the city where you can get a $6 24-hour pass. Pick up a bike in Copley and head to the Charles River Esplanade, the serene park lining the south bank of the river. Follow it toward the iconic Longfellow Bridge to the Museum of Science, Boston, marked by the dinosaur out front. The top-notch museum features interactive exhibits, an IMAX cinema and planetarium shows. For a taste of some of Boston’s best local food options, visit the new Boston Public Market in Haymarket, housing vendors like Bon Me, Mother Juice Company and Union Square Donuts, plus farm stands and bakeries.
Evening
The North End has a touristy reputation, but its winding, narrow streets and overflowing Italian charm are hard to resist. An evening walking tour could include a stroll past the Old North Church, Boston’s oldest surviving church, the Paul Revere House and Copp’s Hill Burying Ground, established in 1659. Cap it off with a sizable slice of thin-crust pizza from Ernesto’s, among the most authentic “Boston-style” pizza you’ll find in town. Or for a taste of New England seafood, head to neighbouring Neptune Oyster, known for its raw bar and rich lobster rolls.
Pick up assorted decadent Italian pastries from either Modern Pastry or Mike’s Pastry, beloved bakeshops where cannolis are served straight-up with ricotta cream, dipped in chocolate chips or pistachios or filled with chocolate cream. Then make your way to Christopher Columbus Waterfront Park, a hidden gem with views of the Boston Harbor.
DAY TWO
Morning
Find breakfast or brunch in the South End at the charming South End Buttery (known for its cupcakes, if you want an early treat), or the cozy Mike & Patty’s, known for their breakfast sandwiches, in the nearby Bay Village. A walk through the South End’s streets reveals charming brownstones and small parks, and you can make your way to the gleaming reflection pool at the Christian Science Center. On Sundays from May through October, the SoWa Open Market on Harrison Ave. features local artisans and vintage vendors, plus food trucks.
Afternoon
Cross the river—via the Red Line or a walk across the Harvard Bridge (known locally as the “Mass. Ave. Bridge”), counting “Smoots” along the way. A tour of Cambridge includes its universities and squares, with a first stop at MIT in Kendall Square, to see the eclectic collections at the MIT Museum and the Frank Gehry-designed Ray and Maria Stata Center, a Kendall Square landmark and photo op.
Then stop for an espresso or gourmet pizza at the sleek Area Four, popular with locals for lunch or an after-work drink. Or, grab a Charles River Tall Tale Pale Ale or one of the numerous creative house beers on tap at Cambridge Brewing Company, a classic Cambridge brewpub serving locally inspired cuisine.
Evening
Head back on the red line, or take a walking tour of Cambridge through Central Square down to Harvard Square, the iconic heart of Cambridge. Dinner options include the trendy modern New England cuisine of Alden & Harlow, known for their creative cocktails, or newly opened sister restaurant Waypoint, featuring a raw bar, pizza and absinthe cocktails.
Post-dinner entertainment abounds, with indie movies showing at the Brattle Theatre, a classic cinema showcasing independent films and throwbacks, followed by espresso or tea at one of Harvard Square’s most beloved cafes, the Middle Eastern-inspired Algiers Coffee House. Or, make your way to The Sinclair music venue, restaurant and bar for rooftop drinks and live music from local and national acts.
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