Boston events October 2019. Things to do in Boston.

Best events for 12 months

Boston events October 2019

Halloween on the farm

October 1 - Nov. 3, 2019
(starts Sept. 7)
22 miles north
A ticket to Connors Farm Corn Maze also includes hayrides, pedal carts, and activities in Danvers. The flashlight maze and haunted farm are only open Friday and Saturday nights, plus a few extra days.

Documentary films

October 2 - 6, 2019
multiple locations
GlobeDocs Film Festival is “focused on telling important stories, large and small.” Films are followed by discussions with journalists and film makers, except the short film series.

Interactive Sleepy Hollow

October 2 - Nov. 3, 2019
(begins Sept. 27)
59 miles east
Dress warmly and head to Old Sturbridge Village for The Sleepy Hollow Experience, a ghoulish guided walk through the countryside featuring encounters with characters like the Headless Horseman. Food is sold before the show and during intermission.

Oktoberfest - Boston

October 4 - 5, 2019
1.5 miles SE
Harpoon Octoberfest features beer, bratwurst, waltzing musicians in lederhosen, and contests in tents at Harpoon Brewery for age 21+.

Horror films in Salem

October 4 - 27, 2019
18 miles NE
Salem Horror Fest invites you “to examine the themes of fear and the American experience within the horror genre” with films and special guests at Salem venues.

Ticket deal $5 (Oct. 11+)

Medieval fair

October 5 - 20, 2019
(begins Aug. 31)
49 miles south
King Richard’s Faire offers medieval food, games, and artisan shops, plus costumed acrobats, battling knights, fire-eaters, jugglers, dancers, and puppeteers in a forest near Carver. Open weekends plus Sept. 2 and Oct. 14 in 2019.

Ticket deal 2 for $49 (September)

Tasting event

October 10 - 13, 2019
Boston locations
The highlight of the The Taste of WGBH Food & Wine Festival is the Chef’s Gala featuring “cuisine from 21 award-winning chefs” plus wine and beer pairings at WGBH for age 21+.

Tasting in Cambridge

October 12, 2019
(4 to 7 p.m.)
2.9 miles west
Local Craft Spirits Festival is a tasting of beer, cider, cocktails, and straight spirits, with live music and food for sale outdoors at 38 Sidney Street in Cambridge for age 21+.

The Artisan Taste

October 12, 2019
5.1 miles west
The Artisan Taste features chef tastings, vintner & brewer tastings, cooking demonstrations, artisan vendors, and live music at WGBH Studios for age 21+.

Brewfest in New Hampshire

October 12, 2019
59 miles north
Sample 100 craft brews from 40 breweries at New Hampshire Brew Fest with food and music in tents at Cisco Brewers in Portsmouth, NH for age 21+.

Apple festival

October 12 - 13, 2019
50 miles west
AppleFest offers a craft and farmer’s market, family entertainment, food, a 5K, and an Oktoberfest with beer garden and live music at Wachusett Mountain.

Columbus Day Parade - North End

October 13, 2019
0.6 miles NE
Watch brass bands, vintage cars, military units, and politicians wind through the North End’s narrow streets in the Columbus Day Parade. Free.

Oktoberfest with street bands

October 13, 2019
(rain date Oct. 20)
3.6 miles west
Enjoy four beer gardens, six stages of entertainment, 50 food vendors, 150 craft vendors, and roving bands that will get you dancing in the streets at Oktoberfest and Honk Parade in Harvard Square.

Brunch + open bar

October 13, 2019
(11 a.m. to 2 p.m.)
5.1 miles west
A ticket to Brunch Bar includes delicious food and beverages (craft beer, cider, cocktails) from 100 restaurants and producers, chef demonstrations, and live music at WGBH Studios for age 21+.

Fenway festival

October 14, 2019
2.2 miles SW
Opening Our Doors has open galleries, art museum admission, art-making, live music, salsa dancing, storytelling, walking tours, and food trucks. Free.

Music festival in Lowell

October 18 - 19, 2019
30 miles NW
Buy a wristband to attend concerts by 50 performing artists at The Town and the City Festival in downtown Lowell. Some venues are for age 21+. Visual art will be displayed in five galleries and museums.

Open art studios

October 18 - 20, 2019
1.1 miles SE
See studios of 100 artists in historic waterfront warehouses during Fort Point Open Studios. Free. Repeats in May.

Prohibition Halloween party

October 18 - 19 and 25 - 26, 2019
43 miles west
Haunted Speakeasy features burlesque and variety acts, dancing to live music in the ballroom, Prohibition Era cocktails, and a 1920s costume contest at historic Bull Mansion in Worcester for age 18+.

Party for charity

October 19, 2019
2 miles west
Eat, drink, dance, and bid in an auction to support hunger relief during Party Under the Harvest Moon at Morss Hall on the M.I.T. campus.

Art on fire

October 19, 2019
51 miles SW
Watch red-hot molten iron fly through the air when industrial art is cast to live music at the Halloween Iron Pour at the Steel Yard in Providence, RI.

Book festival

October 19 - 20, 2019
1.5 miles SW
Boston Book Festival (BBF) celebrates literature and writing with dozens of author talks, seminars, writing workshops, exhibitors and publishers, live music, and kids’ entertainment in and near Copley Square on Saturday and Roxbury on Sunday. Free.

Vegetarian festival

October 19 - 20, 2019
3.9 miles SW
Discover new food items, taste samples, meet producers, hear speakers, and shop at Boston Veg Food Fest at Reggie Lewis Athletic Center. Free.

Rowing race & expo

October 19 - 20, 2019
4.5 miles NW
Watch 9,000 athletes from around the world compete in the Head of the Charles Regatta (HOCR), and visit vendors at the finish line Rowing & Fitness Expo. Free.

Halloween at Stone Zoo

October 19 - 20, 2019
8.2 miles north
Boo at the Zoo features ghoulish games, creepy crafts, costume contests, a trick-or-treat trail, a haunted maze, and pumpkins for animals at Stone Zoo.

Oyster festival

October 19 - 20, 2019
99 miles SE
Wellfleet Oysterfest promises good food, live music, an arts and crafts fair, cooking demonstrations, races for adults and children, kids’ activities, and a shucking contest at Wellfleet on Cape Cod.

Festival of the Dead

October 22 - 31, 2019
21 miles north
Festival of the Dead is a series of events that explore death’s macabre customs, heretical histories, and strange rituals in Salem, led by psychic mediums, paranormal investigators, witches, and warlocks.

Asian film festival

October 24 - 27, 2019
Boston and Cambridge locations
Boston Asian American Film Festival showcases the experiences of Asian Americans on film and supports Asian American filmmakers.

Halloween ball in Salem

October 25, 2019
(7:30 p.m.)
21 miles north
Dance in the Grand Ballroom to pop, party, and goth; see a laser light show and costume contest; eat hors d’oeuvres, and visit the cash bar at Salem Witches’ Halloween Ball at the Hawthorne Hotel in Salem.

Art show

October 25 - 27, 2019
(preview Oct. 24)
1.5 miles SW
See works from 40 galleries at the weekend Boston International Fine Art Show at the Cyclorama. Children age 12 and younger are free.

Halloween radio show

October 25 - Nov. 2, 2019
5.1 miles NW
Hear original adaptations of four creepy tales from around the globe at Tomes of Terror: Beyond Grimm, a radio-style show with on-stage voice acting and sound-effects performed live in Somerville.

Halloween party at Hard Rock

October 26, 2019
0 miles
Hard Rock Halloween Thriller features a DJ playing top 40, hip-hop, and house music at the Hard Rock Cafe near Faneuil Hall for age 21+.

Race in costume

October 26, 2019
1.4 miles SW
Run from Copley Square to Boston Common in your favorite Halloween costume on the The Boston Costume Dash 5K for age 10+, followed by an awards ceremony, costume contest, and after parties.

Beer festival

October 26, 2019
2 miles west
Great Pumpkin Festival features beer, grilled food, and costumes at Cambridge Brewing in Kendall Square. The 8 p.m. session is for age 21+.

Horror movies all night

October 26, 2019
3.7 miles SW
Watch films of terror for 12 hours at the Halloween Horror Marathon, beginning with live music and a costume contest at Coolidge Corner Theatre.

Halloween at F.P. Zoo

October 26 - 27, 2019
3.5 miles SW
Zoo Howl features trick-or-treating, creepy crafts, ghoulish games, costume contests, a haunted maze, and pumpkins for animals at Franklin Park Zoo.

Oktoberfest & blues music

October 27, 2019
44 miles west
Oktoberfest Blues & Brews draws crowds for fall beer, food trucks, scenery, winery tours, and live blues at Nashoba Valley Winery. Bring cash.

Tango dancing

October 30 - Nov. 3, 2019
3 miles NW
Boston Tango Festival includes dance classes, dances with live music, and a Saturday show in Somerville.

Singing competition

October 2019
0 miles
Hear 40 groups compete at the A Cappella Competition at Faneuil Hall Marketplace. Free.

United Nations lunch

October 2019
o.6 miles SW
Celebrate the founding of the United Nations at the $125 UN Day Luncheon, with lunch and a speech by Timothy Edgar, former national security and intelligence official, at the Union Club.

Play bubble soccer

October 2019
2 miles NE
Play a game of soccer while wearing a giant plastic bubble that allows you to bounce safely off other players and roll over during Charity Bubble Soccer at Lopresti Park in East Boston, adult size only.

Psycho with the symphony

October 2019
2.1 miles SW
Watch the great thriller Psycho by Alfred Hitchcock on the big screen as the Boston Pops performs the eerie soundtrack at Boston Symphony Hall.

Beer tasting at the library

October 2019
6 miles north
Taste local craft beer, cider, and restaurant food at Brews for Books, with live music and games in the historic art galleries at Malden Public Library.

Beer & wine festival

October 2019
21 miles north
Taste wine, mead, beer, and cider at the Salem Harvest Fest with music indoors in Salem.

Cranberry festival

October 2019
55 miles SE
Cranberry Harvest Celebration has cooking shows, harvest demonstrations, paddleboat rides, craft and food vendors, kids’ activities, and music in Wareham.

Gruesome comedy

October 2019
3 miles NW
Dress for fallout in the audience when you attend GoreFest, which is part bloodbath, part musical, and all campy at ImprovBoston.

Halloween horror show

October 2019
3.3 miles NW
Billed as a macabre and unsavory night of circus, live music, and gore, Cirque of the Dead includes aerial, acrobatic, and juggling acts plus burlesque at Oberon.

Haunted ship

October 2019
14 miles south
A ticket to Ghost Ship Harbor includes three haunted experiences aboard a ship docked in Quincy. Their fourth offering is a “Paranormal VIP Experience.” Parking is $5. See schedule.

Haunted ski area

October 2019
29 miles NW
Witch’s Woods has seven attractions, including a haunted hayride and a nightmare mansion, at Nashoba Valley Ski Area. See schedule.

Haunted house in 3 cities

October 2019
multiple locations
Factory of Terror includes cutting-edge special effects and actors in professional makeup. See schedule.
  • Fall River
  • West Warwick, RI
  • Worcester

Halloween Pet Parade

October 2019
0 miles
Register your pet for the Halloween Pet Parade and costume contest at Faneuil Hall Marketplace, or just enjoy it as a spectator. Free.

Pumpkin float

October 2019
0.7 miles SW
Fall Pumpkin Float features floating pumpkins, kids’ activities, and music at Boston Common Frog Pond. Bring a hollow pumpkin under 8 inches in diameter. Costumes are welcome.

Halloween party

October 2019
0.9 miles SW
Haunted Hotel at W Boston is billed as the sexiest and funniest Halloween party in Boston, for age 21+.

Family Halloween cruise

October 2019
1.4 miles SE
Halloween Lunch Cruise is a two-hour cruise aboard the Spirit of Boston with a lunch buffet, Halloween music, games, treats, cooking decorating, and a kids’ costume contest departing from World Trade Center.

Doggy Halloween party

October 2019
1.7 miles east
A ticket to family-friendly Howl-O-Ween Pawty includes human snacks, dog treats, a doggy costume parade, and a pet photo, with food for sale at Za Cambridge.

Halloween cruise

October 2019
1.8 miles SE
Sinners & Saints Halloween Cruise is a costume party with DJ music and a cash bar on the Provincetown II, departing from 200 Seaport Boulevard.

Halloween party

October 2019
4.8 miles west
Trick or Treat Halloween Costume Ball promises “New England’s Top DJs” with games, body art, and a costume contest at Garage Boston in Allston.

Family science carnival

October 2019
7 miles west
You’re welcome to wear a costume to A Spooky Science Carnival, where you’ll “learn the science behind some mind-blowing magic tricks and spooky effects while collecting candy” and playing carnival games at Metropolitan Waterworks Museum. Free.

Halloween ghost story

October 2019
12 miles west
An award-winning actor reads the timeless ghost story The Legend of Sleepy Hollow by Washington Irving in the atmospheric boiler house at Charles River Museum of Industry & Innovation in Waltham.

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