Things to do this weekend in Boston      Photo Credit: Boston Discovery Guide

There are so many great things to do in Boston this weekend. Our picks for fun things to do on a budget in Boston this week (October 22 – 24) including Nocturnal Animal Trail, Watch the Head of the Charles Regatta, House Music Dance Party, Pumpkins, Pumpkins, Pumpkins Event at Mass Audobon, Fall Fun on the Farm, Last Weekends of Paddle Boston, and more!

Things To Do This Weekend in Boston 


Nocturnal Animal Trail

Photo Credit: Stevens-Coolidge Place

The Nocturnal Animal Trail will display pumpkins and lanterns, a story walk, and a nocturnal animal scavenger hunt! The trail is self-guided (and not scary!), perfect for children of all ages. Costumes are also encouraged. Among our top picks for things to do in Boston this weekend! 
When: Friday, October 22nd
Where: Stevens-Coolidge House & Gardens, 153 Chickering Road, North Andover
How Much: Free

Haunted Brew Tour at Aeronaut Brewery

Join Aeronaut Brewery as they take you on a journey far from the typical brewery tour you know and love. Tours will depart the taproom every 15 minutes from 7:30pm-11:30pm, and will be sure to give you a fright.
When: Saturday, October 23rd
Where: Aeronaut Cannery, 199 Ashland Street, Everett
How Much: $10

House Music Dance Party

Come to City Hall Plaza for a free, family-friendly house music dance party brought to you by DJ Bruno. Also, the City of Boston is also hosting a pop-up Beer & Wine Garden the evening of the event.
When: Friday, October 22nd
Where: City Hall Plaza, Boston
How Much: Free


Mendon Twin Drive-in Halloween Double Feature

drive in movie

Photo Credit: Time Out

Calling all thrill-seekers, this spooky double feature night at the Mendon Drive-in Movie Theater is just for you! On both Friday and Saturday night, the drive-in will be showing a screening of Halloween followed by Halloween Kills and with Dune, followed by Carnage – pick your poison!
When: Friday, October 22nd and Saturday, October 23rd
Where: 35 Milford St, Mendon, MA
How Much: $30 per vehicle

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Newton Halloween Window Painting

Get in touch with your creative side. The window painting event is open to Newton youth in grades 3-8 each artist is assigned a space on the outside of a merchants’ window in Newton’s town village. Not a painter? Be sure to drive by and see the creativity come to life this season.
When: Saturday, October 23rd
Where: City of Newton, 1294, Newton
How Much: Free

Watch the Head of the Charles Regatta

Photo Credit: Boston Discovery Guide

The Head of the Charles is back! Watch the 17th annual Regatta at the Reunion Village, in a new location this year. Whether you’re a spectator, a competitor, or simply in need of refreshment, the half-way point location has something to offer you. Among our top things to do this weekend in Boston! 
When: Saturday, October 23rd and Sunday, October 24th
Where: New location for 2021: 973 Memorial Drive, Cambridge, MA 02138 
How Much: Admission is $10, drink tickets are $7


Pumpkins, Pumpkins, Pumpkins Event at Mass Audobon

Celebrate the fall harvest by creating your own carved pumpkin with your family group at your own table, playing pumpkin games, and enjoying a fall socially distanced scavenger hunt. 
When: Saturday, October 23rd
Where: Boston Nature Center and Wildlife Sanctuary, Mattapan MA, 500 Walk Hill Street, Mattapan
How Much: $13 – $15

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Fall Fun on the Farm

Photo Credit: The Boston Calendar

Head to the Chestnut Hill Farm the last 4 Sundays of October to enjoy a classic New England fall day. What is a perfect fall day you ask? Apple cider, hayrides, a climbing haystack, live music, scenic walking trails, local vendors & artisans, and a Storywalk.
When: Sunday, October 24th from 12 PM – 4:30 PM
Where: Chestnut Hill Farm, 5 Chestnut Hill Road, Southborough
How Much: $20

Last Weekends of Paddle Boston

Rent a Kayak in Cambridge and Paddle in the heart of the city from our location in Kendall Square and take in all the great views that Boston has to offer. This event makes our list of top things to do this weekend in Boston! 
When: Sunday, October 24th
Where: Paddle Boston, 15 Broad Canal Way, Cambridge
How Much: Free

Free Comedy Show at Beacon Hill Pub

Scared of Monday? Lighten up by heading to a free comedy show. Every Sunday, Beacon Hill Pub offers a free comedy show in the evening.
When: Sunday, October 24th at 8 PM
Where: 149 Charles Street, Boston, MA
How Much: Free

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Know of any other fun things to do in Boston this weekend? Tell us about them by commenting below.

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