The Boston Events Calendar for October 2025 is packed with exciting events: the exciting Head of the Charles Regatta, Boston Fashion Week, and at the end of the month, Halloween events in Boston and nearby Salem (a.k.a. "Witch City").
With an exciting lineup including new shows in the Theatre District, October is an especially exciting month for theater fans.
Looking for Fun Things to Do in Boston in October?
- Fall Foliage Tour from Boston - View spectacular fall foliage in New Hampshire's White Mountains
- Guided Craft Brewery Tour + Snack - Sample up to 12 craft beers; includes transportation
- Ghosts & Gravestones Trolley Tour - Explore the dark side of Boston on this fun tour
Music fans can catch shows at TD Garden, Big Night Live, House of Blues, Paradise Rock Club, and other top concert venues in Boston and Cambridge.
Fall foliage colors appear in earnest in early October, - so enjoy the gold and crimson leaves as they blaze across the city, and join one of the popular fall foliage tours and cruises.
Go on the Fort Point Art Walk, take a sightseeing cruise on Boston Harbor, or just walk around one of the city's historic neighborhoods such as Beacon Hill and the South End, where jack-o-lanterns on doorsteps and our spooky Colonial-era graveyards will remind you Halloween is on its way.
Check out all our top recommendations for fun events & things to do in Boston in October - and plan your visit now!
Top photo: Beautiful October day in Boston's Back Bay neighborhood, (c) Boston Discovery Guide®
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Boston Theater & Shows for October 2025
Top October Shows in Boston's Theatre District
Enter DISCOVERY10 to save 10% on TicketLiquidator & TicketNetwork tickets. Good for purchases made through 12/31/26.
Boston theater during October includes touring Broadway hit shows and musicals , kids shows, and comedy:
- Blue Man Group - Charles Playhouse - Multiple shows all month
Schedule & Tickets
- More Boston Theater District Shows in other months
- Where to have dinner in Boston's Theatre District
Need a Hotel or Short-Stay Apartment in Boston?
Enter your dates to see available hotels and rates. Click through to read reviews and make your reservations.
Booking.comMore about how to save on Boston hotels
Boston Harbor Cruises - October
Tour Boston by boat - the best way to see the city! Check out these fun sightseeing, music, and entertainment Boston Harbor cruises on the Yacht Northern Lights and Schooner Adirondack III:
Popular Cruises
- Northern Lights Sunset Cruise - Grab a refreshments from the bar and then relax as you watch the sun set on this sail around the Harbor, just in time to catch the USS Constitution fire its cannons as the sun dips down past the horizon
- Brunch Cruise on the Northern Lights - Savor a delicious 3-course brunch on this relaxing sightseeing cruise around Boston Harbor
- Boston Harbor Cruise on Northern Lights - Soak up Boston's unique sites and rich history on this comfortable sightseeing cruise around the Harbor - perfect friends and family experience! Food and beverages available for purchase at the bar
Sailing Cruises on the Adirondack III & IV:
- Adirondack Day Sail - Enjoy cool breezes and the afternoon sun on this relaxing sightseeing sail around Boston Harbor and the Inner Harbor Islands - Starts May 1
- Adirondack Sunset Sail - Relax as the setting sun turns the sky brilliant colors - Starts May 1
Mothers Day Cruise
- Mother's Brunch Day Cruise with Live Jazz - Celebrate your mom while you enjoy a delicious brunch and live jazz on this relaxing Harbor cruise - May 11 (don't wait to book - this always sells out!)
Fun Book Your July 4th Cruises Now (because they sell out far in advance!)
- Northern Lights - Harborfest Fireworks Cruise on a 1920's style commuter yacht - July 2
- Adirondack - Harborfest Fireworks Cruise on an 80-foot schooner - July 2
- Adirondack - USS Constitution Turn-Around Cruise with Continental breakfast- July 4
- Northern Lights - USS Constitution Turn-Around Cruise with 3-course brunch - July 4
- Northern Lights - July 4th Fireworks Cruise - 3 hour cruise from Boston featuring Winthrop's spectacular fireworks - July 4
- Adirondack - July 4th Fireworks Cruise - 3 to 3.5 hour cruise from Boston to watch Winthrop's fireworks - July 4
Labor Day Cruise
- Labor Day Fireworks Cruise on Northern Lights - You'll love this crowd-free option for watching the brilliant Labor Day Fireworks over Boston Harbor after a leisurely cruise on this classic commuter yacht - Find out more
Boston Concerts & Shows - October 2025
You'll find a phenomenal number of concerts and shows this month!
Top October Concerts in Boston & Tickets
Enter DISCOVERY10 to save 10% on TicketLiquidator & TicketNetwork tickets. Good for purchases made through 12/31/26.
Top concerts in Boston for October 2025 include Tate McRae, Bryan Adams, Pat Benatar, and Candlelight Concerts:
- Tate McRae - TD Garden - Oct 17
- Bryan Adams, Pat Benatar, Neil Giraldo - TD Garden - Oct 26
- Candlelight Concerts - Multiple dates in October at various locations
October Concerts - Schedules & Tickets
More Concerts & Shows for October
More Boston Concerts & Shows throughout the Year
Salem Halloween: Haunted Happenings Grand Parade
When: Thursday, October 3, 6:30 pm - 8 pm
Location: Downtown Salem, MA around Salem Common and along Hawthorne Boulevard and Essex, Central, and Charter Streets
The Haunted Happenings Grand Parade officially kicks off the season of witches, ghosts, and goblins with a lavish pageant of costumes, music, floats, and entertainment - but that's just the beginning of Salem's Halloween festivities.
More about the Grand Parade and the "Witch City"
Best ways to get to Salem from Boston:
- Guided Day Trip to Salem by Ferry with Witch Museum
- Fast ferry from Boston's Long Wharf to Salem
- Newburyport/Rockport Commuter Rail from North Station
- #450 bus from Haymarket Station in Boston
Check out Halloween in Salem for more about the witch museums.
More to See & Do in Salem:
Boston Discount Passes for Attractions, Tours, Cruises
Why pay full price for top Boston attractions such as the New England Aquarium, Museum of Fine Arts, Plimouth Plantation, Salem Witch Tours, Boston Harbor Cruises, and much more?
Boston Discount Cards are the best deal in town. Select Boston CityPass to see Boston's Top Attractions at a leisurely pace, or choose the GoBoston card (you pick how many days) to see almost 50 attractions, tours, cruises, and day trips.
Whale Watching Cruise Tickets
Join one of the exciting 3-hour Whale Watching Cruises departing from the Downtown Boston Waterfront, and experience the thrill of spotting whales off the coast of Boston.
You'll see magnificent creatures such as Humpback and Finback whales close-up from the deck of your ship, and spot White-Sided Dolphins frolicking in the waters.
These cruises sell out quickly, so don't wait to get your tickets now for this iconic Boston experience!
Oktoberfests in Boston: Where to Celebrate
Three important things to know about Oktoberfests in Boston: 1) Contrary to what the name "Oktoberfest" leads you to believe, many happen in late September with just a few in October; 2) as Boston's craft brewery scene expands, so does the number of Oktoberfests across the city; and 3) they are massive fun!
Fortunately, Oktoberfest fun does continue through October, so you'll still find plenty of fun and brew even if you missed last month's events.
Take advantage of Oktoberfest to check out some new-to-you brewerys, sample some of Boston's best craft beer along with bratwurst, other German foods, pretzels, oompah music, and maybe even do chicken dancing.
Find out more, including where to find the best Boston Oktoberfests this month
Fall Foliage Cruises from Boston
Want to see gorgeous fall foliage along the New England and Eastern Canadian coastlines - and enjoy a few days relaxation and touring?
Fall foliage cruises depart throughout October. You can choose from day-long cruises and overnight trips.
When: Departures throughout October
Cost: Varies according to length of tour and cruise line
More information: Fall foliage cruises
See Gorgeous New England Fall Foliage near Boston
- Fall Foliage Tour from Boston - View spectacular fall foliage in NH's White Mountains
- Coastal Maine Small Group Day Trip from Boston - Offered June - October (go from mid-September - October for fall foliage)
- Full Day Historical Lexington & Concord Tour from Boston - Offered April - early November (go from late September - November for fall foliage)
Boston Lights at Franklin Park Zoo
Franklin Park Zoo transforms into an evening wonderland as more than 55 brilliant outdoor all-new displays take you through fantastic journeys filled with color and light.
You'll discover an ocean tunnel surrounded by sealife, a journey to India with lotus flowers and an ornate palace, animal lanterns depicting monkeys and more, and Chinese lantern scenes with mythical fish.
Not to be missed: a 75-foot enormous glowing fish.
In addition, you can enjoy nightly Chinese classical dance performances including Fan dances.
Get your tickets at the gate (if available), or secure your spot (highly recommended) and also save a little by booking online in advance on the Zoo's website.
Boston Lights dates/hours: Through November 2, 5:30pm-10:30pm (to be confirmed)
Just want to visit the zoo during the day? You can also book or pre-book tickets online for a regular visit (does NOT include the Boston Lights show).
Pru Boo at Prudential Center
Every year, over 50 stores and restaurants at the Shops at Prudential Center sponsor Trick or Treating for Charity, with proceeds going to a non-profit partner.
Kids come dressed in their cutest Halloween outfits and enjoy trick-or-treating, face painting, magic shows, pumpkin decorating, live musical performances, and more.
When: Sunday, October 27, 11-1pm (time to be confirmed)
Where: Prudential Center
Cost: $5 donation per child (12 and under) to purchase a trick or treat bag; all other activities are free. Donations this year will benefit Food Allergy Research & Education. You'll also find lots of non-food treats this year.
More information: Halloween in Boston
Indigenous Peoples Day Weekend Events
Dates: Saturday, October 11; Sunday, October 12; Monday, October 13
You'll find plenty of fun events throughout the weekend, but at this point, none are related to Indigenous People.
This weekend is also when traditionally you'll find big sales in many stores.
Indigenous People's Day Weekend events to check out:
Head of the Charles Regatta 2025
More than 11,000 elite athletes from around the world compete in 60+ events as part of the Head of the Charles Regatta, an exciting 2-day rowing meet held on the Charles River during the last full weekend in October.
If you're visiting Boston this weekend, join the more than 300,000 spectators watching from the bridges and banks of the Charles. Fall foliage along the river is usually near peak on this weekend - so bring your camera!
When: October 17 (8am - 10:30am), 16 (7:45am - 5pm), and 19, (7:45am - 4:30pm) (times to be confirmed)
Where: Charles River between Boston and Cambridge, MA
Cost: Free viewing from most locations. Exceptions include Reunion Village ($15 for one day) and the Eliot Bridge Enclosure ($290 plus online booking fee per day; includes breakfast, buffet lunch, and open bar with beer, wine, and soda)
For more information, including best viewing spots, hotels, Reunion Village & Eliot Bridge Enclosure tickets; transportation (& road closures): Head of the Charles Regatta
Wicked Haunt Fest
A Halloween-themed fall festival and three immersive haunted experiences bring lots of fun and spooky Halloween horror to Boston in the first-ever Wicked Haunt Fest from September 30 - November 2. The fest is open from 4pm - 11pm on most weekdays and 11am - 11pm on weekends. (to be confirmed)
The family-friendly festival features Halloween-themed areas and props, two themed bars and an Octoberfest-style beer garden, seasonal food, huge animatronics, performance spaces, photo ops, pumpkin painting, and costumed vendors.
Immersive experiences include a haunted farm where evil pumpkins infused with dark magic come to life, the shadowy realm of Astray where supernatural chaos reigns and nightmares turn real in a haunted house, a cursed Egyptian tomb filled with a mad Pharaoh and vengeful mummies traps you until you unravel their secrets, and a haunted graveyard filled with murderers and thieves seems to come alive.
The creative mastermind and developer of the event is Lynnfield resident Carl Rugato, known locally for creating traffic-stopping elaborate Halloween displays at his home and professionally for his thematic entertainment productions for Marvel, Jurassic World Live, and Disney on Ice.
Location: Hood Park, 10 Stack Street, Charlestown; closest T station: Orange Line/Sullivan; free parking available for up to 3 hours nearby (you'll see the signs)
See the event website for more information including a few age restrictions, and ticket purchase
Popular Boston Tours & Cruises
Fall Harvest Celebration at Patriot Place
Celebrate the fall cranberry harvest season at Ocean Spray's annual Fall Harvest Celebration at Patriot Place, located adjacent to Gillette Stadium south of Boston.
Highlights of the fun family-friendly day include cranberry bog walks along the nature trail behind Bass Pro Shops, live music, complimentary pony rides, arts and crafts, pumpkin decorating, the New England Patriots Cheerleaders, and lots more.
This year, look for complimentary family photo sessions from 10am - 1:30pm in front of the Harvest Celebration display, and a special Wormtown Brewery pop-up from 12 noon - 4pm in SouthNorth Marketplace.
In North Marketplace, you'll find pickleball, arts and crafts, and pumpkin carving.
Find even more activities, plus all the details on the event website.
When: October 19, 10am - 4pm
Location: Patriot Place
Admission & activities: Free
Columbus Park Fall Festival & Pumpkin Patch
The Columbus Park Fall Festival features a children's parade through the park (watch it or join it), a variety of music and entertainment by local groups, plus family activities including lawn games, pumpkins, and balloon animals in this gorgeous park overlooking Boston Harbor.
Wear your costume!
When: Saturday, October 19, 12 noon - 3:30pm
Cost: Free
Location: Columbus Park, Boston's North End (100 Atlantic Ave - next to the Marriott Long Wharf Hotel)
Public Transportation: Blue Line/Aquarium; about a 3 minute walk north on the Greenway
Cape Ann Artisans Open Studios 2025
Don't miss this wonderful excuse to tour artist studios along the beautiful Rockport and Gloucester coast on Indigenous Peoples Day Weekend!
Local artists and artisans will welcome you to view their paintings, sculpture, mosaics, photography, quilts, pottery, jewelry, and other wonderful creations.
Drive up from Boston for the day (or take the Commuter Rail) - or spend the weekend and go for walks along the beach, dine on lobster dinners, and browse in local boutiques, galleries, and antique shops. View Rockport Hotels
Open Studio Tour: October 11 and 12 at 10am - 5pm
Where: Open Studio Tour map and more information at www.capeannartisans.com - or pick up brochures with route maps at the Cape Ann Chamber of Commerce, the Rockport Information Booth on Rte 127, and at each studio. Look for the Studio Tour banner at each location
More information: Cape Ann Artisans website
Cost: Free
More Indigenous Peoples Day Events in and near Boston
Where to Stay In or Near Boston's North End
Interested in staying in or near Boston's wonderful North End neighborhood, filled with tantalizing Italian restaurants and bakeries?
Consider these welcoming choices:
Find more hotels in or near the North End
More hotels in Boston's North End
Visit Cape Cod on the Fast Ferry in Early October
The easiest and fastest way to get to scenic Provincetown at the eastern tip of Cape Cod is on the "Fast Ferry" - a sleek and luxurious passenger-only catamaran that whisks you to this charming village in only 90 minutes.
Explore Provincetown's many art galleries, chic clothing boutiques, and picturesque lanes at your leisure.
Watch the sun set as you feast on clam chowder and a lobster roll at one of the many restaurants overlooking the water.
But don't wait too long - the Fast Ferry runs only through the Indigenous Peoples Day weekend.
Get Your Fast Ferry Tickets to Provincetown
Find out more about visiting Provincetown
Boston Book Festival
Boston Book Festival brings together a huge lineup of renowned and mostly local writers, scholars, NPR hosts, publishers, and thought leaders.
National Book Award, Newbury, and Pulitzer Prize winners converge in numerous forums, presentations, and discussions organized around topics such as "Legacy of Slavery" and "Women Working It" to celebrate our local culture of reading and ideas, making the Boston Book Festival the largest literary event in New England.
In addition to exhibitions, discussions, sessions for writers, and presentations, you'll normally find live music, booksellers, food, and kids/teen activities.
Boston Book Festival is one of the biggest book fests in the U.S. and there's nothing else quite like it, so don't miss it!
When: October 29 (to be confirmed)
Cost: Free
More information including events, schedules, & locations: website
Fall Foliage Boston Harbor Cruises on the Northern Lights
Combine a scenic fall foliage cruise around Boston Harbor with a delicious brunch or lunch on the elegant Yacht Northern Lights throughout this month and early November.
- Fall Foliage Brunch Cruise on Northern Lights - Enjoy a tasty gourmet brunch, fall foliage, and panoramic views as you cruise around Boston Harbor - Oct 4 through Nov 9
- Fall Foliage Lunch Cruise on Northern Lights - Enjoy a gourmet picnic lunch on this relaxing fall foliage cruise to celebrate seasonal colors - Oct 4 through Nov 9
Fort Point Open Studios
Stop by the FPAC Gallery at 300 Congress Street, pick up a map showing locations where you can see the work of over 100 local resident artists at locations with studios and galleries.
Then stroll around this area of former warehouses and explore the art studios, chat with the artists, and if you're unable to resist, buy a piece or two of memorable art from some of the area's emerging or well-known artists.
Locations include: 249 A and 259 A Street, Factory 63 (63 Melhcer Street), Boston Button Factory (50 Melcher Street), Atlantic Wharf (290 Street), 300 Summer Street, Midway Artists Studios (15 Channel Center Street), and Assemblage Art Space (70a Sleeper Street).
When (to be confirmed) : October 17 - 19
- Oct 17 - Preview from 4pm-7pm (select studios)
- Oct 18 and 19 - 11am - 5pm
Where: Fort Point area of the South Boston Waterfront
Nearest T station: Red Line/South Station; walk across the Congress Street bridge
Parking: Free, in the Central Parking Lot at Binford and A Street
Cost: Free...unless you buy some art!
Where to stay: South Boston Waterfront Hotels
More information: Fort Point Arts Community website; 617-423-4299
Fun Boston Tours for October
More: Sightseeing Tours | Tours for Teens | Kids & Family Tours
New England Patriots at Gillette Stadium - October
Two New England Patriots home games take place at Gillette Stadium during October - so get your tickets now, and get ready to join in the fun!
Enter DISCOVERY10 to save 10% on TicketLiquidator & TicketNetwork tickets. Good for purchases made through 12/31/26.
Where: Gillette Stadium
Getting there: The Patriot Train - plus more ways to get to Gillette from Boston
Where to stay: Hotels near Gillette Stadium
Tickets: Check for great prices, great seats, and sometimes discounts
Bruins on the Ice at TD Garden - Preseason & Regular Season Games - October 2025
Preseason games start in early October, followed by the kickoff of regular season games.
Will this be the year the Bruins win another Stanley Cup?
See the Schedule & Get Your Tickets Now
Save when you use these Ticket Discount Codes:Enter DISCOVERY10 to save 10% on TicketLiquidator & TicketNetwork tickets. Good for purchases made through 12/31/26.
Find Bruins schedule & tickets for all October home games at the Garden
Find Bruins schedule & tickets for all home games
Hotels near TD Garden
Coming to an event at the Garden? Consider spending the night or the weekend at one of these top nearby hotels:
Check out more hotels near TD Garden
Celtics on their Home Court at TD Garden - October Schedule & Tickets 2025
Get your Boston Celtics tickets for November home games, and head over to TD Garden for some fast action on the court.
The Garden's convenient location next to North Station makes it super-easy to get to.
Get ready for plenty of action at the net from Boston's champion basketball team.
Get your tickets now:
Enter DISCOVERY10 to save 10% on TicketLiquidator & TicketNetwork tickets. Good for purchases made through 12/31/26.
Where: TD Garden
Nearest public transportation: Green Line/Orange Line or Commuter Rail to North Station, next to the Garden
Where to stay: Hotels near TD Garden
Best Fall Foliage Tours Departing from Boston
Leaves may still be mostly green in Boston in October, at least during the first couple of weeks - so if you want to see gorgeous foliage, head outside of the city where you'll start to see lots of spectacular New England fall colors.
These luxury 1-day fall foliage tours take you to the best viewing locations in New Hampshire, Maine, and Cape Cod. Sit back and relax while someone else drives and you get to enjoy all the scenery!
More about fall foliage tours leaving from Boston
Newport Mansion Tour from Boston
On this Newport Mansions Day Trip from Boston, you'll visit charming Newport, Rhode Island where the country's richest families built the spectacular waterfront mansions that they called "cottages" during the Gilded Age.
You'll visit two of the most magnificent mansions, and will also have time to walk along the scenic coastal Cliff Walk. You'll see Newport's main attractions during a 1-hour narrated small group driving tour, which includes a visit to the Truro Synagogue. During free time, you can shop, have lunch along the waterfront, and perhaps visit the International Tennis Hall of Fame.
Pickup and dropoff from selected Boston hotels is included.
More Fun Boston Tours
HONK! Street Music Festival in Cambridge & Somerville
When: October 4-6
Where: Somerville & Cambridge
Cost: Free
More information: www.honkfest.org
HONK! Festival of Activist Street Bands fills the streets of Somerville and Cambridge with celebratory music, colorful attire, and lots of fun during the first weekend in October.
Look for a lantern parade around the Davis Square neighborhood along with a band showcase on Friday evening.
On Saturday, 33 brass bands will take over Davis Square all day for a giant music and dance party.
On Sunday, the enormous and always entertaining HONK! parade will meander from Davis Square along Mass Ave to Cambridge followed by an afternoon of HONK! performances in Harvard Square, where the Square's annual Oktoberfest celebration (which attracts 100,000+ revelers) will also be underway.
In addition to the bands, local community groups, artists, and activists join the parade. It's basically a giant street party!
Streets will be blocked and traffic diverted on Saturday from parts of the Davis Square area and on Sunday from large areas surrounding Davis Square, the impacted part of Mass Ave, and Harvard Square.
The resulting backups and gridlock get so fierce and long that you should avoid driving anywhere near these parts of Somerville and Cambridge (and even nearby, due to the backups). If you come to this area, walk or take the T.
Check Honk!'s website for more specific details.
Enjoy Fall Foliage near Your Boston Hotel
Want to enjoy spectacular fall colors right in the city? Boston is filled with trees, and their foliage turns turns brilliant by October.
Here's where to find colorful autumn foliage near these popular hotels:
- Four Seasons Hotel - Cross Boylston Street and enter Boston's Victorian-era Public Garden. Walk around the Lagoon, admire the spectacular autumn colors, and visit the Make Way for Duckling statues.
- Colonnade Hotel - Walk across Huntington Ave to Christian Science Plaza. Find a comfortable bench by the reflecting pool, and enjoy the golden leaves on nearby trees.
- Verb Hotel - Cross Boylston Street and enter The Fens, where you'll find the famous Victory Gardens and Kelleher Rose Gardens.
- Charlesmark Hotel - Walk half a block to Copley Square. Soak up some sun by the pool, explore the weekly Farmer's Market, and tour Trinity Church.
More places to see gorgeous autumn colors in Boston
Tours & Cruises to see Fall Foliage in Boston . . . and Beyond
Museum of Science Exhibits - October
Special Exhibits
- All Aboard! Trains at Science Park - This seasonal exhibit for all ages returns, expanded and enhanced, ready to immerse you in a winter wonderland
- Sustainable Farm - See a first-of-its-kind hydroponic indoor farm
- Arctic Adventure: Exploring with Technology- Fly a virtual drone and become an Arctic explorer
- Exploring AI Making the Invisible Visible: Discover how AI is already part of your life, and examine your choices about how and when you use it
With fascinating permanent exhibits for all ages, there's always something to see, do, and learn. Here are just a few of the most popular: Engineering Design Workshop, Colossal Fossil - Triceratops Cliff, The Light House, Dinosaurs, Hall of Human Life, Animal Sculptures, Live Animal Care Center, a Rock Garden, Mathematica, New England Habitats, Garden Walk & Insect Zoo, Electricity.
Where: Boston's Museum of Science
When: Daily, 9am-5pm; open until 9pm on Fridays
Admission: $31 general museum admission ($26 for kids; children under 3 free; seniors 60+ $27). Reserve your tickets, or get free museum admission when you have a GoBoston Discount card or CityPASS card.
Lawn on D
Lawn on D, a playground for adults (kids are welcome too but this is primarily an adult venue) located behind the Convention Center in the South Boston Waterfront, is where you'll find fun swings with LED lights and comfy seating, pickleball and other games, and music throughout the summer and early fall, along with casual food and wine, beer, cocktails, and non-alcoholic beverages.
Open daily from 7am-11pm from May to October, except when closed for private events (always check their website before going).
Food, drinks, and lawn games available Thursday 3-10:30pm, Friday & Saturday 12 noon-11pm, Sunday 12 noon-10:30pm, with live entertainment by local bands on the weekends.
Swings are open whenever Lawn on D is open.
Rules, in case you're wondering: No dogs, no outside alcohol, no outside food during concession hours.
Another option in this area is to sample one of the many restaurants in the Seaport and Fort Point areas of the South Boston Waterfront.
For Boston Harbor views while you dine, visit a Seaport restaurant. To try the creative cuisine of some of Boston's most innovative chefs, head to a Fort Point restaurant.
Save Big $$$s on Boston Museums and More Top Attractions
Find out how a Boston Discount Card gives you free entrance to museums and lots of other attractions every day while your card is valid - plus you get to go straight to the head of the line.
Boston International Antiquarian Book Fair
Whether you're a serious collector of old books, want to shop for a few holiday gifts, or just like to read, the huge Boston International Antiquarian Book Fair is a must-visit.
With 100+ dealers from the U.S. and Europe, the fair attracts visitors from around the world.
In addition to the rare, collectible, and antiquarian books on exhibit and for sale, you'll also find manuscripts, autographs, maps, children's books, ephemera, atlases, modern first editions, and fine and decorative prints.
If you're coming from out of town, hotels near the Hynes include the Back Bay Hilton, the Mandarin Oriental Boston, the Colonnade, the Charlesmark, the Sheraton Boston, and the Lenox.
When: October 27-29
Where: Hynes Convention Center
Closest T station: N/A
For more information: website -
General public entrance fee: $25 for Friday night preview; free on Saturday and Sunday
Opening Our Doors Festival in Boston's Fenway Neighborhood
Fenway Alliance presents "Opening Our Doors," Boston's biggest single day of FREE arts, cultural, and educational events when its members invite you to 80+ activities, performances, tours, music, and games from 10am - 4pm.
Festivities start on the Mass Ave side of the Christian Science Plaza at the intersection of Huntington Ave and Mass Ave. The kick-off celebration features a Kids Parade with the Hot Tamale Brass Band, performances, and free cupcakes, with fun activities for all ages all day.
Added plus: Free admission to several top Fenway museums, including the Museum of Fine Arts, Isabella Stewart Gardner Museum, and the Mary Baker Eddy Library Mapparium.
When: Saturday, October 9
Where: Multiple locations in Fenway
Cost: Free
More information: Fenway Alliance website - Complete events schedule for Boston's Fenway neighborhood
Fun Events & Activities on the Rose Kennedy Greenway
Weekly events on the Rose Kennedy Greenway begin to wind down in October, but there's still plenty to do and see as leaves begin to turn gold and crimson.
- Chinatown Farmer's Market - Shop for fresh Chinese veggies, fruits, grains, fresh fish, and pastries at this twice-monthly market in the Greenway's Auntie Kay/Uncle Frank Park on July 13 & 27; August 10 & 24, September 14 & 28, and Oct 5 & 19 from 10am - 1:30pm
- Night Shift Beer Garden at Dewey Square Plaza across from South Station. Beer, seltzer, wine plus bites from rotating food vendors. Open Wednesday - Friday from 3pm - 9pm, Saturday 12 noon - 9pm, and Sunday from 12 noon - 7pm
- Trillium Beer Garden in the Wharf District Parks (High Street and Atlantic Ave) featuring draft beers by Trillium Brewing Company and a rotating selection of food trucks. Open Tuesday - Saturday from 3pm - 10pm, and Sunday from 12 noon - 6pm.
- Fountains - You'll find them in 7 different locations along the Greenway - so get ready to splash, wade, and cool off!
- Carousel - Open daily, 11am-6pm. Tickets: $4 (buy online)
- Greenway Food Trucks: A rotation of 20 trucks offer Korean, Jamaican, Indian, Caribbean, Italian, seafood, and other specialties along the Greenway at Night Shift on Dewey Square, the Carousel, Rings Fountain (Milk Street), State Street, the North End, Rowes Wharf Plaza, and Trillium Beer Garden. You'll find them at several locations each day, usually with a total of about 3 trucks per day. You can track the schedule and locations of your favorites here
- Public Art - See new installations by top artists
- Plants & Landscapes - Enjoy the sustainable organic gardens, including the Greenway's Meadow, Beehives, Pollinator Ribbon, Carolyn Lynch Garden with brightly colored flowers, and the Armenian Heritage Park with an abstract sculpture and maze
- Fitness Program - Join any or all of the free fitness classes (many different types) - find the schedule here
More about the Rose Kennedy Greenway
Beacon Hill with a BOO! 
Murders, mysteries, mayhem, and the occasional ghost haunt this special 90-minute walking tour of Beacon Hill featuring (mostly) true tales.
Your guide for this ghoulish annual event, a volunteer with local tour group Boston by Foot, will show you the dark side and even darker alleys of this charming neighborhood.
Wear comfortable walking shoes and your favorite costume!
This tour is Boston by Foot's most popular tour and has been going strong for over 30 years. Don't wait to book, as it fills up quickly.
When: Halloween (plus sometimes other late October dates), multiple time slots, Beacon Hill, Boston
Where: Boston's Beacon Hill neighborhood
For more information: Boston by Foot website
Cost: $20 ($10 for Boston by Foot members) - Purchase tour tickets directly from your guide - no reservations are required.
Interested in a private tour? Boston by Foot will arrange that for you, at private tour rates, given enough lead time - call them at 617-367-2345 for details.
Can't make the Halloween tour? Catch Boston by Foot's "The Dark Side of Boston" tour and hear tales of crime, disease, death, and disaster as you walk around the North End. Takes place earlier in October and throughout the year - check BBF's website for details.
Not Sure about Boston Neighborhood Locations?
This neighborhood map should help you get oriented. You can find a list of top attractions in each neighborhood here.
Need a more details? See our recommendations for free and low-cost Boston maps.
2 Easy Ways to Save BIG in Boston on Tours, Cruises, Admissions
Boston Discount Cards offer you an easy way to save BIG when you take a Boston Harbor cruise or Duck Boat tour, visit Plimouth Plantation, the New England Aquarium, Museum of Science, Museum of Fine Arts, Fenway Park Tour, and more.
Find out which Boston Discount Card is best for you.
More Fun Boston Tours & Cruises
Boston Halloween Pumpkin Float
Put on your Halloween costume and head over to Boston Common's Frog Pond on Sunday, October 16 (to be confirmed) for a Halloween Pumpkin Festival, refreshments, music, and lots of family activities. Halloween costumes are encouraged! This free event takes place from 5-8pm.
Bring an 8 inch or smaller hollowed out carved pumpkin - it will be lit and then floated on Frog Pond for a spectacular display from the glowing pumpkin luminaries. (Note: You MUST hollow it out - otherwise, it will not float!)
More information: Boston Frog Pond website
Greenway Artisan Market
Greenway Artisan Market, sister market to SoWa Open Market (held Sundays in the South End), brings an eclectic mix of hand-made art, music, and locally produced products to Boston.
Look for the sea of white vendor tents - and get ready for some fun shopping, plus good eating at the gourmet food trucks.
With a different mix of vendors present each week, you never know what treasures you'll find! It's a quintessential Boston event.
When: Every Saturday and Sunday through October 31,
11am - 5pm
Where: Rose Kennedy Greenway, near Rings Fountain along the Wharf District parks (look for the Carousel and the vendors' white tents)
Nearest T station: Blue Line/Aquarium, or Orange and Green Lines/Haymarket
Cost: Free (but of course you'll probably be tempted to buy things
More Fun Ways to See Boston
More to Do in Boston in October
More Articles about Things to See & Do in Boston in October
- Interested in getting some exercise while you sightsee? Check out Boston bike tours
- Halloween in Boston - lots of fun things to do
- Fall is just around the corner - and now is a good time to start planning a breath-taking fall foliage cruise
Need a Boston Hotel or Apartment?
Use this handy map from Booking.com to find the perfect place to stay. Just enter your dates to find what's available, see the best rates, and make your reservations.
Booking.com
