Harbor hotels, North End dinners, Freedom Trail mornings.
Three neighborhoods, three classics
Harbor, Beacon Hill and Back Bay, each checked against the hotel’s own site.
Photo: Boston Harbor Hotel via Expedia
Waterfront · Rowes Wharf
The hotel behind the harbor archway, with its own marina and a water taxi across to Logan.
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Photo: The Liberty, a Luxury Collection Hotel, Boston via Google
Beacon Hill · Former jail
An 1851 granite jail at the foot of Beacon Hill, now a hotel with CLINK. and a lobby bar under the rotunda.
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Photo: Fairmont Copley Plaza, Boston via Google
Back Bay · Copley Square
The 1912 grand hotel on Copley Square, home of OAK Long Bar + Kitchen and a resident canine ambassador.
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Start with what you love
Three ways into the city. Pick your lane.
Mark the calendar
Festivals, concerts, races and family events coming up in Boston, checked against the organizers’ own pages.
Boston Lights, the lantern walk at Franklin Park Zoo, runs through Nov 8, 2026, nightly from Oct 1, 5-10:30 pm. Timed tickets; separate from daytime zoo entry.
Event details →Free group bike rides of 9, 2.5 and 0.5 miles plus a festival in Franklin Park on Sunday, Oct 11, 2026, 8:30 a.m.-2 p.m. Loaner bikes with registration.
Event details →The ICA marks 90 years with an exhibition revisiting Warhol, Kusama, Simone Leigh and more, Oct 15, 2026 to Mar 7, 2027 on the Seaport. Hours and admission.
Event details →The Jamaica Pond Lantern Parade returns Saturday, Oct 17, 2026 (rain date Oct 18): thousands of handmade lanterns carried around the pond in Jamaica Plain.
Event details →The 31st Boston Veg Food Fest fills the Reggie Lewis Athletic Center Oct 17-18, 2026 with vegan food vendors, samples, talks and a kids room. Free admission.
Event details →The free Boston Book Festival fills Copley Square on Saturday, Oct 17, 2026, 10 a.m.-6 p.m., with 300+ authors, plus a ticketed Michael Lewis opening night.
Event details →Boston Lyric Opera stages Previn's A Streetcar Named Desire at the Emerson Cutler Majestic Theatre on Nov 5, 6 and 8, 2026. Cast, times and transit tips.
Event details →Boston's Veterans Parade is Saturday, Nov 7, 2026, noon-3 pm, marching from the Boston Public Library on Boylston Street to City Hall Plaza. Free to watch.
Event details →The B.A.A. Boston Half starts and finishes in Franklin Park on Sunday, Nov 8, 2026 at 8 a.m., looping the Emerald Necklace past Jamaica Pond and the Arboretum.
Event details →The SoWa Christmas Market fills the South End Power Station Nov 20-Dec 27, 2026 with 100+ makers and specialty food vendors. $10 entry, kids 12 and under free.
Event details →The holiday trellis lighting at Christopher Columbus Park on the North End waterfront is Monday, Nov 23, 2026, 5-6 pm: music, Santa, cocoa and chowder. Free.
Event details →Boston Ballet dances The Nutcracker at the Citizens Opera House from Nov 27 to Dec 31, 2026, with a live orchestra, a sensory friendly show and matinees.
Event details →Handel and Haydn Society performs Messiah at Symphony Hall on Nov 27, 28 and 29, 2026, its 173rd consecutive year, led by Harry Christophers. Times and tips.
Event details →Free holiday lighting of the play ship at Martin's Park on the Seaport waterfront, Saturday, Nov 28, 2026, 5-6 pm, with Santa arriving by boat. Made for kids.
Event details →The Boston Early Music Festival stages Lampe's mock-opera Pyramus & Thisbe at NEC Jordan Hall on Nov 28 and 29, 2026, with pre-opera talks and a stream.
Event details →Boston Parks lights the Copley Square tree on Monday, Nov 30, 2026, 5-6 pm, and celebrates the grand reopening of Copley Square Park. Free and family friendly.
Event details →Boston's official tree lighting is Thursday, Dec 3, 2026, 6-8 pm on Boston Common: Nova Scotia's gift tree, then the Commonwealth Avenue Mall lights. Free.
Event details →The Boston Pops play 32 Holiday Pops concerts at Symphony Hall from Dec 3 to Dec 24, 2026. Performance times, transit around the station closure and tips.
Event details →The Wasabi Fenway Bowl returns to Fenway Park on Saturday, Dec 26, 2026 at 2 p.m. on ESPN, matching teams from the American conference and the ACC.
Event details →The Boston Wine & Food Festival returns to the Boston Harbor Hotel Jan 22-Mar 6, 2027 with winemaker dinners, tastings and galas on the waterfront. Lineup TBA.
Event details →Dine Out Boston, the city's official restaurant week, runs Feb 20-Mar 7, 2027: prix fixe lunch and dinner menus at participating restaurants, no pass needed.
Event details →Renoir and Love brings 40 paintings, including Dance at Moulin de la Galette, to the Museum of Fine Arts, Boston from Feb 28 to June 13, 2027. Hours, tickets.
Event details →Boston Lyric Opera stages a new Marriage of Figaro at the Emerson Cutler Majestic Theatre on March 12, 14, 19 and 21, 2027. Cast, times and theater tips.
Event details →Boston's St. Patrick's Day and Evacuation Day Parade marches through South Boston on Sunday, March 14, 2027. Free to watch; step-off time to be confirmed.
Event details →The Red Sox open Fenway Park on Thursday, April 1, 2027 against the Cincinnati Reds after a season-opening trip to Seattle. Dates, series and planning notes.
Event details →The ICA brings together ceramics, paintings and photographs by Betty, George and Francesca Woodman from April 15 to Sept 6, 2027. Dates, hours and admission.
Event details →The 131st Boston Marathon runs Monday, April 19, 2027 from Hopkinton to the finish on Boylston Street in Back Bay. Date, viewing tips and what closes.
Event details →Duckling Day is Sunday, May 9, 2027 on Boston Common: free games and music from 10 am, then a noon parade to the Make Way for Ducklings statue. Rain or shine.
Event details →Anime Boston, the Northeast's big anime convention, runs May 28-30, 2027 at the Hynes Convention Center and Sheraton Boston in Back Bay. Badges on sale later.
Event details →Boston Calling returns June 4-6, 2027 at the Harvard Athletic Complex in Allston after a year off. Dates, venue, licensing status and what is still to come.
Event details →Saint Anthony's Feast fills the North End Aug 26-29, 2027 with processions, music and Italian street food, ending in a 10-hour Grand Procession. Free entry.
Event details →From the BostonVacay journal
Guides to help you plan a Boston visit.
Weekend plan
Two days, the essential sights, and how to string them together.
Read guide →City classics
The landmarks, food and traditions most associated with Boston.
Read guide →Off the beaten path
Quirkier stops for a second visit, or for anyone who has done the Freedom Trail.
Read guide →Claim your free listing to update photos, hours and your story, and get found by travelers planning their Boston trip.
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