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Guides
10 best rooftop bars in Boston
Some rooftops call for a reservation and proper shoes. Others call for a burrito. Boston has room for both, along with a brewery greenhouse, a North End roof deck and hotel bars where the harbor does much of the work. Our picks for rooftop bars in Boston include two across the river in Harvard Square. Choose by the kind of evening you want, then confirm that the roof itself is open. A restaurant downstairs can be serving dinner while its outdoor bar is closed for weather or a private party. Felipe’s brings the rooftop down to earth with tacos, burritos and margaritas in Harvard Square. Order something from the wood grill, which cooks chicken, steak and vegetables over hardwood, and take advantage of the seasonal rooftop patio. The drinks use hand-squeezed key lime juice. Come here when you want a casual meal with your drinks, rather than a hotel lounge and a separate dinner reservation. The restaurant’s late hours do not guarantee the roof stays open equally late. Deck 12 sits above the Seaport at YOTEL, with indoor and outdoor seating and views toward downtown and the waterfront. That gives you more flexibility than an entirely exposed roof. It serves evening food during the week and offers weekend brunch, making it an option before a night out or earlier in the day. Reservations are strongly encouraged; choose the time and seating you want rather than arriving at sunset and hoping for the best. Rooftop at The Envoy faces the harbor from Sleeper Street, with lounge seating, fire pits and cocktails above the Seaport. It is a good choice when the view is the main reason you are going. The hotel recommends reservations and accepts limited walk-ins. Outdoor arrangements change with the season, including winter enclosures, so look at the specific experience you are booking. Para Maria, the hotel’s restaurant, is a separate reservation. Daedalus is the Harvard Square choice for a roof-deck dinner with a proper plate of food. The menu includes mushroom risotto, steak frites, shrimp linguine and a bacon-cheddar burger, alongside cocktails, wine and draught beer. Its Mount Auburn Street location puts you a short walk from Harvard Yard. The restaurant currently serves dinner Monday through Saturday and closes Sundays, so do not build a Sunday brunch plan around an old listing. Contessa is the dressier option at the top of The Newbury, overlooking the Public Garden and Back Bay. The room was designed by Ken Fulk, and the menu follows Northern Italian cooking, with dishes such as ricotta gnudi and tortellini in brodo. The bar serves Negronis and Martinis, with an extensive Italian and French wine selection. Think of this as a rooftop restaurant where you can have a drink, rather than a casual open-air beer deck. Reserve if dinner is part of the plan. Mia is the roof deck inside Umbria on Hanover Street, serving cocktails and appetizers intended for sharing. It gives a North End evening somewhere to continue after dinner, but it requires more planning than simply walking upstairs. Mia is reservation-only and 21-plus, with a dress code that excludes hats, sandals, shorts and athletic wear. Book Mia specifically, since a table at Umbria and a roof-deck reservation are different things. The Overlook occupies the third floor of Legal Sea Foods Harborside, with a broad view across Boston Harbor. This is the rooftop to consider when you want seafood as well as drinks: the setting puts the water directly in front of you, rather than somewhere beyond a wall of buildings. Legal’s three floors have different uses, including a separate private-event level, so confirm that your booking is for The Overlook. Rooftop@Revere has lounge furniture, an outdoor bar and private cabanas above the Theater District. Its view takes in Back Bay, making it an option for drinks before or after plans downtown. The venue strongly encourages reservations on busy evenings and weekends, and even hotel guests are subject to capacity. If you want a cabana, check that booking’s terms separately. A casual table for two and a reserved cabana are different commitments. Cunard Tavern’s roof deck, The Layover, brings a walk-up bar and harbor views to East Boston. The menu leans toward tropical drinks, including rum cocktails, with beer, wine and food available as well. The roof deck has its own schedule, distinct from the dining room. Public service is seasonal, while private events can use the space year-round. Confirm rooftop availability before crossing over for it, especially outside the warmer months. Dorchester Brewing Company has the Hopservatory, a four-season rooftop greenhouse that lets you keep the upstairs plan when the weather turns. The brewery serves its own beers alongside cider, wine, cocktails and nonalcoholic options, with food from M&M BBQ. You can also visit the Museum of Bad Art inside the building for free. Beer, barbecue and a gallery visit make a fairly complete afternoon without requiring a second address. When booking, select the rooftop or ask the venue to confirm it. A general restaurant reservation does not necessarily buy you a seat upstairs. Check any minimum spend, cancellation terms and weather policy before paying a deposit. If the forecast sends you indoors, our Boston speakeasy guide has another set of places to settle in for a drink.
18 unique things to do in Boston: a local’s guide
A free afternoon in Boston can end with live jazz, a lobster roll or a bag of clothes bought by weight. You can also spend it looking at stolen paintings’ empty frames, climbing above the trees or learning to make your own dinner. These unique things to do in Boston give you choices beyond another lap of the same few streets. Most are in Boston, with a Cambridge shopping stop and an outdoor excursion in Canton clearly marked. Pick a couple near each other and leave time between them. The North End suggestions work together; a museum in the Fenway and a brewery in Hyde Park need more planning. The Isabella Stewart Gardner Museum arranges paintings, furniture and other objects around an interior courtyard. Its galleries also hold empty frames left after the 1990 theft. Take time to look at the rooms themselves rather than treating the visit as a checklist of paintings. Advance tickets are recommended, and the museum is closed on Tuesdays. Thursday evenings are free, with tickets released two days ahead. Phinista’s Fenway café is at 96 Peterborough Street. Order the Iced Saigonese for phin-dripped coffee topped with salted cream foam, or turn the stop into breakfast with a bánh mì. Its menu also includes pandan and ube drinks. Pair this with a Fenway museum visit or a walk through the neighborhood; Peterborough Street is in the Fenway, not the South End. Wally’s Café Jazz Club has been part of Boston since 1947. The small room at 427 Massachusetts Avenue brings students and experienced musicians onto the same bandstand, with live music every night. Check the club’s schedule for the evening you want, then leave room in the plan to stay and listen. The performance is the reason to come. The Freedom Trail connects the Revolutionary-era sites; the Innovation Trail follows developments in science, medicine and technology across Boston and Cambridge. Its map includes the telephone, anesthesia and instant photography, with museum stops along the way. Both can be walked independently. Choose a section that interests you rather than assuming you need to finish the whole route in one outing. The Garment District in Cambridge has vintage clothing, contemporary secondhand pieces and costumes at 200 Broadway. Its By the Pound department makes shopping more of a rummage: you choose the clothes, then pay by weight. Give yourself time to look through the racks as well. For more shops worth browsing, our unusual shopping guide covers stationery, gifts, books and vintage finds. The Sports Museum’s guided tour takes visitors through exhibits on levels five and six of TD Garden. It covers the city’s teams and wider sporting history, including the Boston Marathon. This is a separate experience from an arena tour, which has more restricted availability. Check the museum’s tour calendar before going; games, concerts and other events can affect access. Bova’s Bakery gives a North End walk an easy destination: bread, Italian pastries and savory food at the corner of Salem and Prince streets. It operates around the clock, so you can make the bakery stop before the rest of the neighborhood wakes up or after dinner. Buy something to take with you, then continue toward the waterfront. A box for later is also a reasonable plan. At Neptune Oyster, the lobster roll comes hot with butter or cold with mayonnaise on a toasted brioche roll. Pick the version you actually want; there is no requirement to conduct a regional loyalty test at lunch. The Salem Street restaurant also serves oysters and other seafood. Check its current seating arrangements before arriving, and keep any plans during a wait close enough to return when called. Charter Street Park is a small North End stop with an ornamental garden and seating. It gives you somewhere to pause between the neighborhood’s busier streets. Chris of Boston Hidden Gems recommended the park in our original guide. Pair the break with a walk toward the Harborwalk, rather than expecting a large park with sports facilities or a playground. TreeTop Adventures is the out-of-town option on this list, in Canton. Its high-ropes courses include bridges, ladders and zip lines, with different difficulty levels. The courses are for ages seven and up, with additional participation rules to check before booking. Use the park’s reservation calendar for operating dates and session options. Allow time for the trip instead of treating it as a quick downtown stop. The Arnold Arboretum has 281 acres of trees, paths and hills in Jamaica Plain and Roslindale. Lilacs are a spring reason to go, but the collections give you something to look at throughout the year. Check the visitor map before choosing an entrance. A short loop near the visitor center and a longer hill walk are different outings, especially with children or limited time. Walk Charles Street for shops and cafés, then look up toward the neighborhood’s brick houses and narrow side streets. Acorn Street may be the photograph you came for, but leave residents’ doorsteps and entrances clear. Finish toward the Public Garden, or follow our historic Boston day out for a plan that includes the Athenaeum, dinner and a drink. Roundhead Brewing in Hyde Park occupies the Powerhouse at Westinghouse Plaza. Beer, pizza, ping-pong and skee-ball make it a place where a group can settle in for more than a tasting. Look at the brewery’s event calendar for music and community gatherings. Its regular opening days are Wednesday through Sunday, so save this outing for later in the week. Selfup’s Boston cooking classes take place at 19 Kingston Street. The schedule includes options such as pasta, sushi and steakhouse meals, and participants eat what they make afterward. Choose by the menu and class date, then check any dietary restrictions before paying. Beer and wine are available to buy, but are not included in the class ticket. At Commonwealth Avenue and Dartmouth Street, the Vendome Fire Memorial honors the nine Boston firefighters killed in the 1972 disaster. The memorial includes a firefighter’s coat and helmet and an account of the events. Pause to read it when walking the Commonwealth Avenue Mall. This is a place to remember the people who died, and a reminder that the city’s history includes more than its celebrated buildings. The Citizens Opera House hosts touring Broadway productions and Boston Ballet in a restored theater on Washington Street. Choose a performance from the venue’s own calendar, then follow its ticket link to the authorized seller. If the building interests you more than a particular show, historical tours are offered when the production schedule allows. They are not available year-round, so book an announced date. Haunted Boston runs walking tours that combine local history with ghost stories. Its public tour season runs from March through November, with advance purchase required; private tours can be arranged year-round. Treat the supernatural accounts as stories, then enjoy seeing familiar streets after dark. Check the booking details for your date and the meeting instructions before heading out. USS Constitution at the Charlestown Navy Yard is a commissioned Navy ship, with active-duty sailors aboard. Visiting the ship is free, while the neighboring USS Constitution Museum is a separate stop. Adults need physical photo identification for ship entry, and everyone goes through security. Check the ship’s opening schedule before crossing town, since a walk around the Navy Yard and a visit aboard are not the same thing. For admission discounts and outings that cost nothing, use our free and cheap things to do in Boston guide before buying tickets. Reserve the activity with a fixed start time first, then fit food and a walk around it.
Get to know Boston
4 Boston-area gangster hangouts with brutal backstories
The Winter Hill Gang once conducted business in a Somerville garage that now welcomes a church congregation. On Prince Street, Mafia associates talked inside an apartment while the FBI recorded them. In South Boston, a couple opened a liquor store and soon found themselves being told to hand it over by men threatening to kill them. Boston mob headquarters were a first-floor apartment on Prince Street, a liquor store on Old Colony Avenue whose owners kept saying no, and two garages, one later filmed by state police and one now used as a church. The North End headquarters with microphones in the walls 98 Prince Street, North End Gennaro Angiulo and his associates used a first-floor apartment at 98 Prince Street as a Mafia headquarters. From January 19 to May 3, 1981, the FBI recorded the conversations through hidden microphones, and a concealed camera outside photographed people coming and going so the voices on the tapes had faces. Those recordings became evidence in federal court. An FBI supervisory special agent later told the Senate that one slice of the Angiulo family's numbers business was bringing in $30,000 a day. For nearly a year before those tapes, the FBI could not get video of the address. People nearby reported suspected investigators to the Angiulos, often with a license plate, and they were usually right. Across 103 days of pictures, someone brought the brothers a new car or a new face on nearly every day. Agents hid a camera in a vehicle and changed that vehicle every evening. They were not spotted. The liquor store Whitey Bulger refused to take no for 295 Old Colony Avenue, South Boston Stephen Rakes and Julie Rakes opened Stippo's Liquor Mart in 1983. Julie later used the name Julie Rakes Dammers. In January 1984, James "Whitey" Bulger, Stephen Flemmi, and Kevin Weeks let themselves into the family's South Boston home. Bulger said they had been paid to kill Rakes and had decided to buy the store instead. Rakes said it was not for sale. Bulger said he would be their partner. Rakes refused that, too. They were back that evening. They sat at the kitchen table, showed a gun and a switchblade, and threatened to kill him. Flemmi picked up the couple's one-year-old daughter, stroked her hair, and said it would be a shame for her not to see her father again. Bulger handed Rakes a paper bag with roughly $65,000 and promised $25,000 more, which he later refused to pay. Flemmi said the store had new owners. The First Circuit's account of the extortion lays out that visit. The Rakeses held out for weeks, left for Florida, and came back still trying to keep the business. Julie's uncle, Boston police detective Joseph Lundbohm, asked FBI agent John Connolly for help. Connolly told Bulger. Bulger then told Rakes to make Lundbohm back off, and the family signed the title over. The store was at 295 Old Colony Avenue. Public records show Kevin Weeks bought the property. In May 1986 the building was sold to Weeks, Bulger, and another person, and South Boston Liquor Mart, Inc. was set up to do business there. The shop was also known as Columbia Wine and Spirits and by its original name, Stippo's Liquor Mart. A federal forfeiture appeal is where the address and the 1986 company are traced. The garage where the afternoon visitors weren't coming for repairs Lancaster Street, near the former Boston Garden Mechanics had the Lancaster Street Garage in the morning. Most days around 1:30 p.m., Bulger and Flemmi arrived, Bulger in a black 1979 Chevy that he pulled into a bay, and the visitors came for them rather than for a repair. Dick Lehr and Gerard O'Neill describe that routine in Black Mass. George Kaufman, who had operated Marshall Motors in Somerville as a front for Howie Winter, ran this garage for the two of them. They had moved the meetings downtown, a short walk from 98 Prince Street and a couple of blocks from Boston Garden. Massachusetts State Police filmed Bulger there in 1980. The Justice Department still has the footage. The Winter Hill headquarters that became a church 12 Marshall Street, Somerville Marshall Motors, at 12 Marshall Street in Somerville, was the garage they left behind. Kaufman ran it as a front for Howie Winter, and the back room is where Winter, John Martorano, and Bulger met. The Boston Globe described the place as the Winter Hill Gang's office for gambling and loansharking. James Sousa was killed there in October 1974, after other gangsters worried he would talk to police about a botched plan to rip off a dentist with a fake gold sale. A mobster, remembering the room years later, said, "There was blood everywhere." A church bought the building in 2008. In May 2026 the Globe found it open as Greater Works Church of God Somerville. Reporter Danny McDonald went to a Sunday service and found purple seats, screens welcoming worshippers, and a mural of people being baptized in a river. Rev. Collin Green led the prayers. After the service he brought up Howie Winter on his own. "It's changed," he said. "It's not that way. God is in the building."
What the colors of the Zakim Bridge lights mean
Green on the Zakim does not automatically mean the Celtics. Purple does not have one permanent meaning either. The Zakim Bridge lights change for holidays, memorials, and awareness campaigns, and the same color can stand for several unrelated things in a single year. MassDOT publishes a dated lighting calendar. Match the night to the entry, check that the Zakim is one of the bridges listed, and you have a better answer than guessing from the color alone. That last part matters. The state schedules several bridges on the same page. An entry for the Longfellow or the Braga is not automatically an entry for the Zakim. Where to check the Zakim Bridge lights The MassDOT bridge lighting schedule lists the occasion, color, date, and participating bridges. Use the current year, especially if the photo you are looking at has been reposted without a date. The 2026 calendar is a useful demonstration of why a universal color key would fail. Green has already been used for St. Patrick’s Day, Boston Legacy Football Club, and Living Donation Week. Blue has appeared for World Parkinson’s Day and for the twenty-fifth anniversary of September 11. Those are not competing theories. They are different nights. A blue bridge photographed in April cannot explain a blue bridge photographed in September. Two September nights this year make the point. On September 11 the Zakim was blue. On September 13 it was green, and that night the Zakim was the only bridge on the list. Same week. Different colors. Different reasons. Multi-color displays can be easier to tell apart, though the date still matters. The schedule names combinations as well as single colors. Read the full line before attaching a meaning to a picture, particularly when the occasion is a memorial or a health campaign. Who gets to decide MassDOT’s bridge lighting policy, dated November 14, 2023, says special displays express the agency’s official views. The bridges are not a public billboard and not an open platform for anyone’s message. A change needs approval from the department’s Office of the General Counsel and the transportation secretary’s concurrence. The policy covers state and federal holidays, other national observances, and public commemorations and celebrations at the national, state, or local level. The calendar can still move after that approval. A screenshot is useful evidence of an earlier plan. The live page is the better place to check what is scheduled now. The Zakim is one of several state bridges with programmable lights. The policy also names the Longfellow, Fore River, Kenneth F. Burns, and Braga bridges. Matching colors across the state can be one coordinated observance, not a coincidence. Why blue looks familiar Blue is also the bridge’s ordinary night look. Color Kinetics, which worked with MassDOT on the LED system, describes the design as blue-lit towers with the cables picked out in white. The company cites architect Miguel Rosales, who wanted a formal entrance to Boston. The LED system was unveiled in December 2012. It replaced older metal halide lights that had been on the bridge since it opened in 2002 and had grown dim. The new fixtures can hold the familiar blue or shift for a listed occasion. The lighting is not a new coat of paint. It is a programmed change. Blue by itself is therefore not enough to identify a tribute. Check whether a special blue display was on the calendar for that night before assigning it a meaning. Read the date before the symbolism For an old photograph, establish the date before looking up the color. For a night you have not seen yet, check the calendar again close to the date. If the page has no matching entry for the Zakim, leave the occasion unconfirmed rather than borrowing one from another month or another bridge. The fastest route to the answer is the least dramatic: date, bridge name, calendar line. Boston has other lights with a code, including the weather beacon on the old Hancock. This one usually comes with a schedule.