Best of October: 30+ Boston Events We’re Loving This Month

October is here and it is one of our favorite months in Boston! The cool crisp air, foliage, fall treats, Halloween and more all make this a very fun and special time in the city. Some of our picks for special events this October are listed below.  We hope these inspire some special fall fun outings this month!!


October 1-6

Oktoberfest at Lansdowne Pub
Thursday, October 3, 4pm
Enjoy a Sam Adams Octoberfest in a souvenir signature mug; stein hoist contest

Mayhew’s Fall Grand Tasting 
Thursday October 3, 5-7pm
Enjoy a wine tasting and delicious Charcuterie at Mayhew’s Fort Point Wine Shop

First Fridays
Friday, October 4, 10pm
Enjoy DJ and late night kitchen at the Hard Rock Cafe

Harpoon Brewery Octoberfest 
Friday and Saturday, October 4& 5th
Harpoon’s largest festival of the year

Boston Food Truck Festival
Saturday, October 5, 11-5
Rose Kennedy Greenway
Food trucks, trillium beer, local artisans, kids activities and more!

Cheeky Monkey Octoberfest
Saturday October 5, 4pm
live entertainment, local beer, themed food and more!

SOWA Open Market
Sunday, October 6, 10am
Local art, food, beer garden, food trucks, shopping, lawn games and more!

Harpoon Brewery Dogtoberfest 
Sunday, October 6, 11am
run/walk, costume contest, beers for the people and special dog friendly treats for the pups

Back Bay Beer Festival 
Sunday, October 6, 12-3pm
Food truck inspired foods, giveaways, beer tastings and more!



October 7-13

Boston Public Market at Seaport
Wednesday, October 9, 12pm
Last month of the farmer’s market in Seaport Common

Celebrate 10 years of the Greenway
Thursday, October 10, 5:30pm
Specially commissioned dance performance in and around the colored lights of the Rings Fountain

Blue Man Group
Charles Playhouse
Friday, October 11, 7:30pm
always a favorite!

Fenway Neighborhood Food Tour
Saturday, October 12, 10-12pm
Iconic restaurants in and around Fenway

2019 Last of WGBH Food & Wine Festival
Saturday, October 12, 1pm
Grand Tasting Event with a range of culinary experiences; tickets

New England Chocolate Festival
Saturday, October 12, 10-6pm
The Cyclorama at the Boston Center for the Arts

Wizards and Witches Dinner
Sunday, October 13, 5pm
Fairmont Copley Plaza
Family friendly Harry Potter themed magically inspired dinner

Brass Brunch Sundays at W Boston
Sunday, October 13, 10-2pm



October 14-20

Fall Wine Dinner at Back Bay Social Club
Wednesday, October 16, 6:30pm; tickets
mulled wine welcome treat; 3 course dinner with 3 featured wines

Astronomy After Hours
Friday, October 18, 7:30pm
Museum of Science

Fall Pumpkin Float 2019
Frog Pond
Friday, October 18, 5pm
Hundreds of illuminated jack o lanterns float on water

Movies on the Harbor- “Nightmare Before Christmas”
Friday, October 18, 8pm
The Anchor Boston

5th Annual Brunch Battle at Gather
Saturday October 19, 12pm
Vote for Brunch Battle Champion
Proceeds to benefit Community Servings

SOWA Open Market
Sunday, October 20, 10am
Local art, food, beer garden, food trucks, shopping, lawn games and more!

2019 City Winery Harvestfest
Sunday, October 20, 3pm

October 21-31st

Fall Harvest Dinner at Bar Boulud
Tuesday, October 22, 7pm
Special one night only seasonal five-course dinner with wine pairings

Boston Public Market at Seaport
Wednesday, October 23, 12pm
Last month of the farmer’s market in Seaport Common

Boston Public Market Harvest Party
Thursday, October 24, 5:30pm
Food Vendor samples, brewery and cider pop ups, live music, dancing and more; tickets

Cambridge Cider Social 
Benefit for ALS research the ALS Therapy Development Institute
Local cideries and bakeries including Bantam Cider, Portico Brewing, Far from the Tree and more!
Tickets; use code datenightdiscount to receive $10 off tickets!

MFA Late Nites
Friday, October 25, 8pm
small plates, dancing, DJ, beer garden and more

Napa in New England
Friday, October 25, 6pm
Four Seasons Hotel

Haunted Hotel Halloween Party at W Boston
Saturday, October 26, 9pm

Halloween Puppy Patio Brunch at Loretta’s Last Call
Saturday, October 26, 12pm

Cask n Flagon Halloween Bash
Saturday, October 26, 10pm

Day of the Dead Halloween Party
Libery Hotel Boston
Saturday, October 26, 8pm

Basic Witches Halloween Brunch 
City Tap Boston
Saturday, October 26, 11am

The Pumpkin Palooza
The Lawn on D
Saturday & Sunday, October 26 & 27

Hands On: Sherry Cocktails!
The Hawthorne
Sunday, October 27, 7pm

Loretta’s Halloween Hoedown
Thursday, October 31, 10pm
live music, costume contests, specialty cocktails

The Harp’s Halloween 2019
Thursday, October 31, 9pm




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