Boston events October 2019. Things to do in Boston.

Best events for 12 months

Boston events October 2019

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.

Charity wine tasting

October 4, 2019 (6 to 8:30 p.m.)
0.4 miles NW
“Sip fine wine, spirits, craft beer, and cider” at Wine and Wishes, with “gourmet food pairings, a lively auction and raffle, live music, and inspiring mission moments” at City Winery Boston.

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+.

Celebrate a jazz legend

October 5, 2019 (7:30 p.m.)
multiple locations
John Coltrane Memorial Concert is a tribute to an early American jazz saxophonist and composer that includes a film, panel discussions, and concerts at Northeastern University and nearby.

Family-friendly party

October 5, 2019 (12 to 4 p.m.)
10 miles west
The Century Party promises games and activities for all ages, including wagon rides, live music, archery, and a food and beer tent at Gore Place in Waltham.

Food truck festival in Quincy

October 5, 2019 (12 to 6 p.m.)
10.6 miles south
Shop from 20 food trucks, hear five bands, and check out the kids’ stage at the Food Truck & Music Festival on Coddington Street in Quincy. Free.

Medieval fair

October 5 - 20, 2019
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 and October 14, 2019.

Science-themed run

October 6, 2019 (9 a.m.)
1.2 miles west
Hosted by the Museum of Science, the 5K Sci-K Fun Run begins at Fiedler Field on the Charles River Esplanade and is followed by an awards ceremony, food, beverages, and science activities. Science-themed costumes, dogs, and strollers are welcome.

Tasting event

October 10, 2019 (7:30 p.m.)
Boston locations
Chef’s Gala is the highlight of The Taste of WGBH Food & Wine Festival, featuring “cuisine from 21 award-winning chefs” plus wine and beer pairings at WGBH for age 21+.

Wine tasting in Waltham

October 11, 2019 (7 to 10:30 p.m.)
12 miles west
Taste 10 wines that are each “paired with a work of fine art,” eat hors d’oeuvres, attend Q&A sessions with wine professionals and artists, and join a silent auction at Palate2Palette: An Evening of Wine & Art at Charles River Museum of Industry & Innovation for age 21+.

Tasting event

October 12, 2019 (7 to 10 p.m.)
5.1 miles west
“More than a dozen talented chefs go head to head competing in 10 categories” to earn your vote at Food Fight, with international dishes, beverage tastings, and cooking demos at WGBH Studios for age 21+.

The Artisan Taste

October 12, 2019 (1 to 4 p.m.)
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+.

Music festival in Marshfield

October 12, 2019
30.7 miles SE
Trampled By Turtles (bluegrass & folk rock) and The Ballroom Thieves (rock-infused folk) are headline acts at Flannel Jam, an all-ages event with hot cider, s’mores, craft beer, doughnuts, and a kids’ hay maze at Marshfield Fairgrounds.

Brewfest in New Hampshire

October 12, 2019 (noon)
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+.

Columbus Day Parade - North End

October 13, 2019 (1 p.m.)
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 (12 to 6 p.m.)
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. Rain date Oct. 14.

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), chef demonstrations, and Celtic music at WGBH Studios for age 21+.

Doggy Halloween party

October 13, 2019 (1 to 2:30 p.m.)
11 miles NW
A ticket to family-friendly Howl-O-Ween Costume Pawty includes human snacks, dog treats, a doggy costume parade, and a pet photo, with food for sale at Mighty Squirrel Brewing Co. in Waltham.

Free art & culture festival

October 14, 2019 (10 a.m. to 4 p.m.)
2.2 miles SW
Opening Our Doors promises “art exhibitions and activities, cultural experiences, music, and dance performances” in Fenway venues. Guide. Free.

Pumpkin float

October 18, 2019 (5 to 8 p.m.)
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.

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.

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.

Tasting in Cambridge

October 19, 2019 (4 p.m., VIP 3:30)
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+.

Comedy show

October 19, 2019 (7:30 p.m.)
10.4 miles NE
Boston Comedy Blowout features six stand-up comedians at Lynn Auditorium.

Beer & wine festival

October 19, 2019 (2 to 8 p.m.)
21 miles north
Taste wine, mead, beer, and cider at the Salem Harvest Fest with music indoors in Salem.

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.

Singing competition

October 19 - 20, 2019
0 miles
Hear 40 groups compete at the A Cappella Competition at Faneuil Hall Marketplace. Free.

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.

Apple festival

October 19 - 20, 2019
50 miles west
AppleFest offers a craft and farmer’s market, live music, kids’ entertainment, and food trucks at Wachusett Mountain.

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. This event goes plastic-free in 2019.

Free harbor cruise

October 20, 2019
1.3 miles SE
Sign up for a Free Harbor Tour provided by “Save the Harbor,” departing from Rowes Wharf. Free.

Festival of the Dead

October 21 - 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.

Halloween on the farm

October 21 - Nov. 3, 2019
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 in October (plus Oct. 6 & 31).

Irish musical

October 23, 2019 (7:30 p.m.)
30 miles NW
Tony Award winner Once is an emotionally captivating musical about love and loss, with live folk music, dancing, and humor at Lowell Memorial Auditorium.

Discount tickets

Gruesome comedy

October 23 - 31, 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.

Thanksgiving comedy

October 23 - Nov. 10, 2019
1.4 miles SW
A culturally sensitive drama teacher creates a student pageant to honor both Caucasian pilgrims and Native Americans but offends both in The Thanksgiving Play, a “wickedly funny satire” written by a female member of Sicangu Lakota nation, at Lyric Stage Company of Boston.

Discount tickets

Gospel music biography

October 23 - Nov. 10, 2019
10 miles north
Marie and Rosetta tells the story and features the music of Sister Rosetta Tharpe, whose ferocious guitar playing and swinging gospel music inspired rock-n-roll, at Greater Boston Stage Company in Stoneham.

Discount tickets

United Nations lunch

October 24, 2019 (noon)
o.6 miles SW
Celebrate the founding of the United Nations at the $120 UN Day Luncheon, with lunch and a speech by Timothy Edgar, former national security and intelligence official, at the Union Club.

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.

Evening cruise on Boston Harbor

October 24 - Nov. 2, 2019
0.5 miles SE
View the city’s skyline and harbor on an evening cruise aboard the Northern Lights, which has a bar and departs from 60 Rowes Wharf.

Haunted ski area

October 24 - Nov. 2, 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.

Discount tickets

Ghost stories in a mansion

October 25, 2019
10 miles west
Tour the beautiful rooms of an 1806 mansion, stopping along the way to hear spooky tales on Frightful Fridays at Gore Place in Waltham.

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.

Prohibition Halloween party

October 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+.

Discount tickets

Classical music

October 25 & 27, 2019
2.6 miles SW
Boston Baroque performs works by Mozart and Haydn at the New England Conservatory.

Discount tickets

Horror films in Salem

October 25 - 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. The following venue has discount tickets:

Haunted house in 3 cities

October 25 - 31, 2019
multiple locations
Factory of Terror includes cutting-edge special effects and actors in professional makeup. See schedule.
  • Fall River
  • West Warwick, RI (closed Oct. 4 & 20)
  • Worcester

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.

Discount tickets

Charles River cruise

October 25 - Nov. 10, 2019
1.3 miles NW
Take a 90-minute Fall Foliage Cruise departing from Lechmere Canal Park at CambridgeSide Galleria Mall.

Discount tickets

Live musical: Willy Wonka

October 25 - Nov. 17, 2019
3.7 miles SW
Based on Roald Dahl’s story about a world-famous candy man and his quest to find an heir, Willy Wonka features enchanting songs about a delicious adventure at Wheelock Family Theatre.

Discount tickets

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+.

Halloween Pet Parade

October 26, 2019 (12 to 2 p.m.)
0 miles
Enter your pet in the Halloween Pet Parade and costume contest at Faneuil Hall Marketplace, or just enjoy it as a spectator. Free.

Evening jazz cruise

October 26, 2019 (board 7:15 p.m.)
0.5 miles SE
The Evening Jazz Cruise features music by Benjamin Young Quartet and 1.5 hours of Boston Harbor views aboard the vintage Northern Lights, departing from Rowes Wharf. Beverages and snacks are sold onboard.

Discount tickets

Halloween party

October 26, 2019 (9 p.m.)
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 26, 2019 (boarding 11 a.m.)
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.

Race in costume

October 26, 2019
1.7 miles west
Run along the Charles River Esplanade in your favorite Halloween costume on the The Boston Costume Dash 5K for age 10+, followed by an awards ceremony, costume contest, and after party.

Beer festival

October 26, 2019 (uncertain)
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 (11:59 p.m.)
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.

Halloween horror show

October 27 & 31, 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, burlesque, and juggling acts with a live band and dancing at Oberon for adults.

Discount tickets

Mind-reading comedy

October 27 - Dec. 29, 2019
0.4 miles SW
Master mentalist Jon Stetson entertains with a funny show that “blends the art of mystery with the study of psychology, the predictability of human nature, and the power of intuition” at Omni Parker House.

Discount tickets

Halloween ghost story

October 30, 2019 (7 to 8 p.m.)
12 miles west
An award-winning actor tells “ghostly traditional New England tales, from silly to spooky” at Ghost Stories by Candlelight in the atmospheric boiler house at Charles River Museum of Industry & Innovation in Waltham.

Spooky opera

October 30 - 31, 2019
20 miles north
Watch a seance with the dead that goes horribly wrong at The Medium: A Halloween Event, a “classic 1940s opera performed by world-class singers with reimagined staging” at Peabody City Hall.

Discount tickets

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.

Interactive Sleepy Hollow

October 31, 2019 (7:30 p.m.)
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. Closed Mondays and Tuesdays.

Discount tickets

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