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Holiday Events and Things to do in Brookline, MA

Search for something you love or check out popular events in your area.

Selling fast
Fall Falladays Festival
Tomorrow at 4:30 PM
Watertown Town · 130 Arsenal Yards Blvd
Selling fast
Fall Falladays Festival
Tomorrow at 4:30 PM
Watertown Town · 130 Arsenal Yards Blvd
Lanterns in the Woods (Previously Lanterns in the Village)
Fri, Oct 9, 6:30 PM
South Salem · Salem High School
Lanterns in the Woods (Previously Lanterns in the Village)
Fri, Oct 9, 6:30 PM
South Salem · Salem High School
Westwood Harvestfest 2026
Sat, Oct 3, 10:00 AM
Massachusetts · Martha Jones School
Westwood Harvestfest 2026
Sat, Oct 3, 10:00 AM
Massachusetts · Martha Jones School
Sales end soon
17th Century Fall Faire at the Rebecca Nurse Homestead
Saturday at 1:00 PM
Tapleyville · The Rebecca Nurse Homestead
Sales end soon
17th Century Fall Faire at the Rebecca Nurse Homestead
Saturday at 1:00 PM
Tapleyville · The Rebecca Nurse Homestead
Halloween Night of Mystique: Psychic Readings, and an Immersive Sound Bath
Fri, Oct 30, 6:30 PM
Riverview · ZEST The Collective
Halloween Night of Mystique: Psychic Readings, and an Immersive Sound Bath
Fri, Oct 30, 6:30 PM
Riverview · ZEST The Collective
4th Annual Friends of Breakheart Halloween Pet Parade
Sun, Oct 18, 11:00 AM
North Saugus · Breakheart Reservation
4th Annual Friends of Breakheart Halloween Pet Parade
Sun, Oct 18, 11:00 AM
North Saugus · Breakheart Reservation
Dr. Feverdream's Halloween Experiment: an all-ages Haunted House
Fri, Oct 23, 6:00 PM + 1 more
Wedgemere · Winchester Unitarian Society
Dr. Feverdream's Halloween Experiment: an all-ages Haunted House
Fri, Oct 23, 6:00 PM + 1 more
Wedgemere · Winchester Unitarian Society
2026 Easton Festival of Trees
Sun, Nov 29, 11:00 AM
Massachusetts · Easton Country Club
2026 Easton Festival of Trees
Sun, Nov 29, 11:00 AM
Massachusetts · Easton Country Club
Hale-o-ween 2026
Sat, Oct 24, 1:00 PM + 1 more
Massachusetts · Hale
Hale-o-ween 2026
Sat, Oct 24, 1:00 PM + 1 more
Massachusetts · Hale
Pumpkinfest: Beers & Cocktails Sampling
Fri, Oct 23, 7:00 PM
Brighton · Broken Records
Pumpkinfest: Beers & Cocktails Sampling
Fri, Oct 23, 7:00 PM
Brighton · Broken Records
CHBE's Annual Harvest Festival
Sat, Oct 3, 12:00 PM
Roxbury · 95 R Thornton St
CHBE's Annual Harvest Festival
Sat, Oct 3, 12:00 PM
Roxbury · 95 R Thornton St
Sales end soon
Harvest Moon Festival, Salem, Massachusetts!
Saturday at 10:00 AM
Derby Wharf · Polish Legion of American Vets
Sales end soon
Harvest Moon Festival, Salem, Massachusetts!
Saturday at 10:00 AM
Derby Wharf · Polish Legion of American Vets
Sales end soon
Apple Picking 2026 Season
Saturday at 10:00 AM + 5 more
West Medway · Fairmount Fruit Farm
Sales end soon
Apple Picking 2026 Season
Saturday at 10:00 AM + 5 more
West Medway · Fairmount Fruit Farm
BLINGO Bingo
Tue, Dec 1, 6:00 PM
Massachusetts · Easton Country Club
BLINGO Bingo
Tue, Dec 1, 6:00 PM
Massachusetts · Easton Country Club
Halloween Craft & Fun Fair
Sun, Oct 18, 10:00 AM
Medford Square · Condon Shell
Halloween Craft & Fun Fair
Sun, Oct 18, 10:00 AM
Medford Square · Condon Shell
Sales end soon
Little Artists: Pumpkins & Paint
Saturday at 11:00 AM
Downtown · Winthrop Center
Sales end soon
Little Artists: Pumpkins & Paint
Saturday at 11:00 AM
Downtown · Winthrop Center
Pappas Way Oktoberfest
Thu, Oct 1, 5:00 PM
South Boston Waterfront · Pappas Way
Pappas Way Oktoberfest
Thu, Oct 1, 5:00 PM
South Boston Waterfront · Pappas Way
Castle Island Oktoberfest
Sat, Oct 17, 11:00 AM
South Boston · Castle Island Brewing Co. - South Boston
Castle Island Oktoberfest
Sat, Oct 17, 11:00 AM
South Boston · Castle Island Brewing Co. - South Boston
Family Fall Fest at New Covenant School
Sat, Oct 24, 11:00 AM
Six Moon Hill · 7 Clematis Rd
Family Fall Fest at New Covenant School
Sat, Oct 24, 11:00 AM
Six Moon Hill · 7 Clematis Rd
Boston Fall Festivals and Events
Fri, Oct 2, 10:00 AM
Beacon Hill · 139 Tremont St
Boston Fall Festivals and Events
Fri, Oct 2, 10:00 AM
Beacon Hill · 139 Tremont St

Trends in Brookline

Explore more trends

Explore more trends

Frequently asked questions about Brookline

What are the best festival events to attend?

According to Eventbrite, the best festival events are:

Lanterns in the Woods (Previously Lanterns in the Village)

Westwood Harvestfest 2026

17th Century Fall Faire at the Rebecca Nurse Homestead

Halloween Night of Mystique: Psychic Readings, and an Immersive Sound Bath

Which events are currently trending in Brookline?

The trending searches this month in Brookline are:

celtics watch party

coolidge corner

jewish single events

Which festival events are coming up?

Discover the best festival events happening soon – you don't want to miss them:

Fall Falladays Festival

Harvest Moon Festival, Salem, Massachusetts!

Apple Picking 2026 Season

Little Artists: Pumpkins & Paint