The Boston Events Calendar for October 2023 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.

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 2023

Wilbur Theatre
Wilbur Theatre in Boston's Theatre District

Top October Shows in Boston's Theatre District

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Schedule & Tickets

Find all shows for October 

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.

More about how to save on Boston hotels

Boston Harbor Cruises - October

Boston sailing and yacht cruises

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:

Valentine's Day Cruises

Popular Cruises on the Northern Lights:

  • 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!  Refreshments are available for purchase at the bar
  • Sunset Jazz Cruise on Northern Lights - End your weekend on the perfect note by grooving to live jazz as you watch the ever-changing sunset colors as the sun sets behind Boston's city skyline

Gift Card

Boston Concerts & Shows - October 2023

Boston Concert Schedule - October
Jose Gonzalez and yMusic playing at Berklee Performance Center - Photo taken by Ben Stas and courtesy of

You'll find a phenomenal number of concerts and shows this month!

Top October Concerts in Boston & Tickets

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Top concerts in Boston in October 2023 are just starting to be announced, so keep checking to see more:

  • Lady A - MGM Music Hall - Oct 20

October Concerts - Schedules & Tickets

More Concerts & Shows for October

More Boston Concerts & Shows throughout the Year  

Salem Halloween:  Haunted Happenings Grand Parade

Salem MA Halloween Events

When:  Thursday, October 7, 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: 

Check out Halloween in Salem for more about the witch museums.

Where to stay in Salem

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.

Save BIG with Go Boston discount card
CityPASS Boston discount card at

Whale Watching Cruise Tickets

Whale watching cruise
Tail of a humpback whale, seen on a whale watching cruise - Photo credit:

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!

Oktoberfest in Boston: Where to Celebrate

Harpoon Brewery in South Boston Waterfront
Friends celebrating Oktoberfest - Credit:

Three important things to know about Oktoberfests in Boston:  1) Contrary to what the name "Oktoberfest" leads you to believe, most happening late September 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're a lot of fun! 

Don't miss this chance to sample some of Boston's best brews along with bratwurst, other German foods, pretzels, oompah music, and maybe even chicken dancing.

Find out more, including where to find the best Boston Oktoberfests this month

Chef's Table Food & Wine Pairing Events at Bonde

Chefs Table food & wine pairing at Bonde, with Gilbert Cellars' Grüner Veltliner paired with Peruvian/Lima cuisine by Chef JuanMa Calderón from Celeste (Union Square, Somerville)
Chefs Table food & wine pairing at Bonde, with Gilbert Cellars' Grüner Veltliner paired with Peruvian/Lima cuisine by Chef JuanMa Calderón from Celeste (Union Square, Somerville)

Get ready to savor superb small-production American wines paired with cuisine from top local restaurants when Bonde Fine Wines' owner/sommelier Bertil Jean-Chronberg teams up with chefs at some of the area's best restaurants to present weekly wine and food pairings.  You'll enjoy a flight of four special wines accompanied by small plates of complementary food as you learn about the 5 key things to consider when doing your own pairings. Here's the lineup for October:

  • Oct 5:  Explore various styles of Pinot Noirs and their perfect food pairings
  • Oct 12:  Pairing wine & various types of wood-fired Neopolitan-style pizza with guest Chef Brian Kevorkian from Cambridge's Source
  • Oct 19:  New American wines paired with new American cuisine from Chef Conor Dennehy of Cambridge's Talulla Restaurant
  • Oct 26:  Biodynamic wines from top American winemakers paired with complementary food

Bonde also offers 45-minute wine and food tastings on Sunday afternoons; see the website for details

Location:  54 Church Street, Harvard Square, Cambridge
Time:  Wednesday evenings, 7pm-9pm
Cost:  $85; sessions limited to 8 participants; reservations required
More information and reservations: Bonde website

More about where to find wine tastings in Boston 

Fall Foliage Cruises from Boston 2023

Fall foliage along the New Hampshire Coast
Lobster boats in Kennebunkport, Maine on a fall morning - Photo credit: iStock/DougLemke

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

Find more cruises from Boston

Boston Lights at Franklin Park Zoo

Celestial lights at Franklin Park Zoo's Boston Lights festival
Celestial lights at Franklin Park Zoo's "Boston Lights" festival

Franklin Park Zoo transforms into an evening wonderland as more than 55 brilliant outdoor displays take you through the rainforest, a celestial universe, a bamboo forest with pandas, the ocean, a canopy of Asian lanterns, and much more.  Not to be missed:  a 66-foot rose-lined corridor (planning to propose? this could be the perfect spot) and an even longer octopus tunnel with blinking eyes.

Get your tickets at the gate (if available), or secure your spot and also save a little by booking online in advance on the Zoo's website.

Boston Lights dates/hours:  Through October 20, 6pm-10:30pm
Cost:  Online tickets for same-day purchase start at about $26, with children's and family prices available.

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

Pru Boo Boston Halloween event at Prudential Center in October
Trick or treating at Pru Boo

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 30, 11-1pm.
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 Bosto

Indigenous Peoples Day Weekend Events

Dates:  Saturday, October 7; Sunday, October 8; Monday, October 9

Last year, then-acting Boston Mayor Kim Janey signed an executive order that officially changed the second Monday of each October (already an official 3-day holiday weekend) from Columbus Day to Indigenous Peoples Day, and the name change appears to be on its way, although slowly, to being made official for the entire state by the Massachusetts Legislature. 

You'll find plenty of fun events throughout the weekend (at this point none are related to Indigenous People, but hopefully that will change in time), including big sales in many stores.

Indigenous People's Day Weekend events to check out:

Head of the Charles Regatta

Head of Charles rowers
Head of the Charles

When:  October 20(8am - 10:30am), 21 (7:45am - 5pm), and 22, (7:45am - 4:30pm) (to be confirmed)
Where:  Charles River between Boston and Cambridge, MA
Cost:   Free viewing from most locations.  Exceptions include Reunion Village ($10 for one day) and the Eliot Bridge Enclosure ($175 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, transportation (& road closures):  Head of the Charles Regatta

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!

Popular Boston Tours & Cruises

Fall Harvest Celebration at Patriot Place

Freshly harvested cranberries - Photo credit: Bruxelle
Freshly harvested cranberries - Photo credit: Bruxelle

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.  You can even test your soccer skills at the Revolution Fan Zone.

When:  October 15, 10am - 4pm
Location:  Patriot Place
Admission & activities:  Free
More information

Columbus Park Fall Festival & Pumpkin Patch

Columbus Park in Boston's North End
Columbus Park in Boston's North End

When:  Saturday, October 15, 12 noon - 3pm  
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
Cost:  Free

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!

Boston Pizza Festival at City Hall Plaza

Boston Pizza Festival - July Event
Mouth-watering pizzas - Photo credit:

Boston's expansive City Hall Plaza turns into a giant picnic ground when the Boston Pizza Festival returns on October 1-2 bringing pizza, entertainment such as pizza tossing shows and live music, adult and other beverages, and games to this family-friendly celebration of summer. 

Fans devoured over 27,000 pizzas by top local pizza makers such as Pizzeria Regino, Bricco, Antico Forno, and Serafina at Boston's most recent event.  Pizza slices and beverages sold on site.

Tickets:  TBD (children 5 and under free)
More info:

Cape Ann Artisans Open Studios

Painting by Deb Schradieck at Rockport Open Studios
Painting by Deb Schradieck at Rockport Open Studios

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 7 and 8 at 10am - 5pm  (to be confirmed)
Where:  Open Studio Tour map and more information at - 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

More hotels in Boston's North End

Visit Cape Cod on the Fast Ferry in Early October

Provincetown beach in October
Provincetown beach in 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

Fun Events & Activities on the Rose Kennedy Greenway

Splash fountain on the Greenway
Splash fountain on the Greenway

Rose Kennedy Greenway continue through early fall: 

  • Greenway Food Trucks:   Over 35 trucks offering specialties ranging from Korean to Summer Shack's seafood to fresh seafood in Dewey Square, the Carousel, Rings Fountain (Milk Street), State Street, Rowes Wharf Plaza, and Trillium Beer Garden.  You'll find them at several locations each day, usually with a total of 5-7 trucks per day.
  • Farmers Market in Dewey Square run by Boston Public Market offering fresh produce, meat, cheese, breads and pastries, ice cream, and more.  Open Tuesdays and Thursdays 11am - 4pm
  • Chinatown Farmer's Market in Chin's Park (area of the Greenway by Chinatown).  Look for fresh Chinese vegetables, squash, and fruits; fresh seafood; and staples such as rice, flour, nuts, honey, noodles, beans.  Open every other Saturday (October 8 & 22), 10am - 2pm
  • 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 onsite food trucks.  Open Thursday and Friday 2-10pm, Sat 12 noon-10pm, Sunday 12 noon-6pm.
  • City Winery Open Air Wine Garden on Dewey Square across from South Station, serving their locally-crafted wine on tap plus with craft beer and cider by Harpoon Brewery along with a menu of fresh wraps, cheese boards, and snacks.  Open Wed and Thurs 4-9pm, Friday 4-10pm, Sat. 1-9pm, Sunday 11am-7pm.
  • Public Art - See new installations by Rob "ProBlak" Gibbs, Cheryl Wing-Zi Wong, Juan Travieso, and Yu-Wen Wu.
  • 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-8pm.  Tickets: $4.

More about the Rose Kennedy Greenway

Greenway walking tour and map

Boston Book Festival

Copley Square, site of the Boston Book Festival
Copley Square, site of the 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
More information including events, schedules, & locations:  website

Fall Foliage Boston Harbor Cruises on the Northern Lights 2023

Fall Foliage Boston Harbor Cruise on the Northern Lights
Boston Light on Little Brewster Island in Boston Harbor - the first lighthouse built in North America in 1716 and restored in 1783, after being destroyed by the British in 1776

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.

Fort Point Open Studios

Fort Point Open Studio exhibit
Fort Point Open Studio exhibit

When: (to be confirmed)
Oct 13 Preview from 4pm-7pm (select studios)
       Oct 14 and 15 from 12 noon - 6pm

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!
More information:  Fort Point Arts Community website; 617-423-4299

Stop by the FPAC Gallery at 300 Congress Street, pick up a map showing locations where you can see the work of about 60 local resident artists at locations with studios and galleries, including:  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).

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. 

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!

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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 2023

New England Bruins October schedule at TD Garden in Boston
Photo courtesy of Dan4th Nicholas

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 DISCOVERY 10 to save 10% on TicketLiquidator & TicketNetwork tickets

Find Bruins schedule & tickets for all October home games at the Garden

Find Bruins schedule & tickets for all home games

Hotels near TD Garden

If you're coming to an event at the Garden, spend the night or the weekend at one of the nearby hotels, such as the stylish Boxer (shown in photo):

Boxer Hotel, top choice near Boston's TD Garden

More top hotels near the Garden:

Check out more hotels near TD Garden

Celtics on their Home Court at TD Garden -   October Schedule & Tickets

 Boston Celtics playing at TD Garden

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:

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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

Boston fall foliage tours and cruises

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

Enjoy Fall Foliage near Your Boston Hotel

Want to enjoy brilliant fall colors right in the city?  Boston is filled with trees.  Here's where to find colorful autumn foliage near these popular hotels:

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.

Four Seasons Hotel - Cross Boylston Street and enter Boston's Victorian-era Public Garden.  Admire the spectacular autumn colors and visit the  Make Way for Duckling statues. 

More places to see gorgeous autumn colors in Boston

Tours & Cruises to see Fall Foliage in Boston . . . and Beyond

Newport Mansion Tour from Boston

Bannister's Wharf in Newport, Rhode Island
Bannister's Wharf in Newport, Rhode Island

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.

Find out more

More Fun Boston Tours

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.

Save BIG with Go Boston discount card
CityPASS Boston discount card at

HONK! Street Music Festival on Indigenous Peoples Day Weekend

Photo of HONK Festival band - coming to Boston on Indigenous Peoples Day Weekend
HONK! musicians in Davis Square, Somerville

When: October 6-8
  Somerville & Cambridge
Cost:   Free 
More information:

HONK! Festival of Activist Street Bands fills the streets of Somerville and Cambridge with celebratory music, colorful attire, and lots of fun during Indigenous Peoples Day weekend. 

Look for a gigantic bands showcase on Friday evening, continuous free performances and art-making activities in Davis Square all day on Saturday, and the enormous and always entertaining HONK! parade down Mass Ave in Cambridge followed by an afternoon of HONK! performances in Harvard Square, where the annual Oktoberfest celebration (which attracts 100,000+ revelers) is also underway.

Check their website for more specific details:

Museum of Science Exhibits - October

Museum of Science Boston Exhibit
Museum of Science Butterfly Garden - Photo credit: Ted

Special Exhibits

  • New England Climate Stories - Meet fascinating New England animals
  • All Aboard! Trains at Science Park - Visit miniature landscapes with fantasic model trains - through January 16
  • Gaia - View our planet in a new way through UK artist Luke Jerram's artwork with NASA images of Earth's surface
  • Mental Health: Mind Matters - Get insights into understanding mental health through this interactive exhibit

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, Cosmic Light, Dinosaurs, Arctic Adventure, Hall of Human Life, Live Animal Care Center, Mathematica, Exploring AI, Natural Mysteries, New England Habitats, Project Vaccine.

Where:   Boston's Museum of Science
When:   Daily, 9am-5pm; open until 9pm on Fridays
Admission:  $29 general museum admission ($24 for kids; children under 3 free).  Get free museum admission when you have a GoBoston Discount card or Boston CityPASS card. 
Imax Theater and Planetarium:  Additional fees apply

Lawn on D

Lawn on D summer events

Lawn on D, a playground for adults (kids are welcome too but this is mostly 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, bocce and other games daily from 7am-11pm throughout October (except for when the Lawn closes for private events - always check before going).  However, concessions selling food and beverages end on October 2.

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.

Boston International Antiquarian Book Fair

When:  November 10-12 (General public portion; paid preview on Nov 10) (to be confirmed)
Where:   Hynes Convention Center
Closest T station: N/A
For more information: website -
General public entrance fee:  $TBD for Friday night preview; free on Saturday and Sunday

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, 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.

Opening Our Doors Festival in Boston's Fenway Neighborhood

Big arts celebration in Boston's Fenway for Indigenous Peoples Day

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 8, 2023 
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

Splash fountain on the Greenway
Splash fountain on the 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.

  • Greenway Food Trucks:   Over 35 trucks offering specialties ranging from Korean to Summer Shack's seafood to frozen hoagies in Dewey Square, Congress Street, the Carousel, Rings Fountain (Milk Street), State Street, and Rowes Wharf Plaza, and Trillium Beer Garden.  You'll find them at 2-6 locations each day, and although the number of trucks vary each day, the number of locations and trucks is the biggest on Thursdays.
  • Farmers Market in Dewey Square run by Boston Public Market offering fresh produce, meat, cheese, breads and pastries, ice cream, and more.  Open Tuesdays and Thursdays 11am - 4pm
  • Boston Calling Block Parties - Live music and drinks from Blue Moon Brewing, Vizzy Hard Seltzer Canada, Topop Chico Aqua Mineral, and more.  Thursdays, 5pm-8pm, Dewey Square.
  • 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 onsite food trucks.  Open Thursday and Friday 2-10pm, Sat 12 noon-10pm, Sunday 12 noon-6pm.
  • City Winery Open Air Wine Garden on Dewey Square across from South Station, serving their locally-crafted wine on tap plus with craft beer and cider by Harpoon Brewery along with a menu of fresh wraps, cheese boards, and snacks.  Open Wed and Thurs 4-9pm, Friday 4-10pm, Sat. 1-9pm, Sunday 11am-7pm.
  • Public Art - See new installations by Daniel Gordon in the Fort Point Channel Park
  • Fountains - You'll find them in 7 different locations along the Greenway.
  • Carousel - Open daily, 11am-8pm.  Tickets: $4.
  • Greenway Fitness Programs:  Free fitness and yoga classes from local studios; must preregister

More about the Rose Kennedy Greenway

Greenway walking tour and map

Beacon Hill with a BOO! 

Haunted walking tour for Halloween in  Boston's Beacon Hill

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!

When:   6pm on October 31, Beacon Hill, Boston - arrive 10 minutes before tour starts 
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?

Map of Boston showing central neighborhoods

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

Boston Halloween Parade and Pumpkin Festival
Pumpkins for the Halloween 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

More Fun Ways to See Boston

More to Do in Boston in October

Events and things to do in Boston in October

More Articles about Things to See & Do in Boston in October

Need a Boston Hotel or Apartment?

Use this handy map from to find the perfect place to stay.  Just enter your dates to find what's available, see the best rates, and make your reservations.