Massachusetts

25+ Great Fall Things to Do with the Family This Weekend

Fall is in the air and this weekend brings so many great fairs and festivals, making it the perfect weekend to hit the road for some outdoor fun. From the Topsfield Fair to the Salem Food Truck Festival and everything in between (including Harpoon's Dogtoberfest), we’ve gathered two dozen fun things to add to your weekend plans.

Friday, Sept. 28 

Boston Parks Summer Fitness Series

Join the Boston Public Health Commission, Boston Parks and Recreation Dept. and Blue Cross Blue Shield of Massachusetts as they kick off the summer of 30 free outdoor fitness classes each week in and around the city. These free classes take place throughout Boston’s 18 neighborhoods and two dozen parks all summer long. Today try Bootcamp at 6:30 a.m. at Christopher Columbus Park in the North End or a walking group at 10 a.m. at Moakley Park in South Boston.

Deerfield Fair

New England’s oldest family fair returns for its 142nd year of agricultural family fun. Tickets are $10 each for ages 13 and over. Children under 12 are free. 8 a.m. to 10 p.m., 34 Stage Road, Deerfield, NH.

Opening Day at the Topsfield Fair

Don’t miss this annual tradition as the Topsfield Fair is celebrating its 100th anniversary this year when it opens its gates from today until early October. 1-11 p.m., 207 Boston St., Topsfield. 

Harpoon Octoberfest

Hoist a pint with your friends at Harpoon Brewery’s biggest festival of the year. Tickets are $25 and include a souvenir pint cup and one beer ticket. 5:30-11 p.m. (doors close at 9:30 p.m.), Harpoon Brewery, 306 Northern Ave., Boston.

Citizens Bank Weekly Cornhole Tournament

The weekly cornhold tournament, sponsored by Citizens Bank returns for summer.The first eight teams of two will compete for “Lawn Bucks.” All the fun starts at 6:45 p.m.. Sign up for free at the Citizens Bank kiosk starting at 6:30 p.m. The Lawn on D, 420 D St., Boston. 

Saturday, Sept. 29

Deerfield Fair

New England’s oldest family fair returns for its 142nd year of agricultural family fun. Tickets are $10 each for ages 13 and over. Children under 12 are free. 8 a.m. to 10 p.m., 34 Stage Road, Deerfield, NH.

Boston Parks Summer Fitness Series

Join the Boston Public Health Commission, Boston Parks and Recreation Dept. and Blue Cross Blue Shield of Massachusetts as they kick off the summer of 30 free outdoor fitness classes each week in and around the city. These free classes take place throughout Boston’s 18 neighborhoods and two dozen parks all summer long. This morning enjoy a walking group at 8 am. At Franklin Park in Dorchester, yoga at 9:15 a.m. at Franklin Park, Dorchester, yoga at 10 a.m. at Healy Playground, Roslindale or bootcamp at 11 a.m. at Almont Park in Mattapan.

Topsfield Fair

Don’t miss this annual tradition as the Topsfield Fair is celebrating its 100th anniversary this year. 9 a.m. to 9 p.m., 207 Boston St., Topsfield. 

Breakheart Fall Festival

Enjoy pumpkin decorating, take-home crafts, scarecrow stuffing, touch-a truck, lawn games and a whole lot more at the annual, free Breakheart Fall Festival. Breakheart Reservation, Saugus.

Smolak Fall Festival

Grab the family and head to Smolak Farm for its Annual Fall Children’s Festivals every weekend through Oct. 28. 10 a.m. to 5 p.m., Smolak Farms, 315 South Bradford St., North Andover.

King Richard’s Faire

New England's largest and longest running Renaissance Festival is back for another season filled with entertainment, rides, games and more. Open weekends through Columbus Day. 10:30 a.m. to 6 p.m., 235 Main St., Carver.

Salem Food Truck Festival

The Salem Food Truck Festival returns with 45 of the areas top food trucks. From grilled cheese to whoopie pies, there’s something for everyone. 11 a.m. to 6 p.m., Salem Common, Salem, MA.

Greenway Open Market

Celebrating its eighth season, this open-air artisan market features talented area artists, crafters and independent designers. 11 a.m. to 5 p.m., Rose Kennedy Greenway, 185 Kneeland St., Boston.

Berklee Beantown Jazz Festival 2018

Enjoy world-class music on three stages, food and drink, arts, crafts and more at Boston’s biggest, free annual block party and public contest. Noon to 6 p.m., Columbus Avenue, west of Massachusetts Avenue, for six blocks to Burke Street.

Bites + Brews with Remnant Brewing

Out and about today? Stop by the Remnant Brewing pop-up on the plaza alongside rotating BPM food vendors at the Boston Public Market. Noon to 8 p.m., Boston Public Market, 100 Hanover St., Boston.

Harpoon Octoberfest

Hoist a pint with your friends at Harpoon Brewery’s biggest festival of the year. Tickets are $25 and include a souvenir pint cup and one beer ticket. 1-7 p.m. (doors close at 5:30 p.m.), Harpoon Brewery, 306 Northern Ave., Boston.

Sunday, Sept. 30

Deerfield Fair

New England’s oldest family fair returns for its 142nd year of agricultural family fun. Tickets are $10 each for ages 13 and over. Children under 12 are free. 8 a.m. to 10 p.m., 34 Stage Road, Deerfield, NH.

Topsfield Fair

Don’t miss this annual tradition as the Topsfield Fair is celebrating its 100th anniversary this year. 9 a.m. to 9 p.m., 207 Boston St., Topsfield.

SoWa Open Market

The SoWa Open Market is back for its 15th season. Enjoy this weekly celebration of local artisans, farmers, food trucks, brewers, musicians and more. While you’re there enjoy a selection of local brews, stay for a lawn game and enjoy live music. 10 a.m. to 4 p.m., 530 Harrison Ave., Boston.

Smolak Fall Festival

Grab the family and head to Smolak Farm for its Annual Fall Children’s Festivals every weekend through Oct. 28. 10 a.m. to 5 p.m., Smolak Farms, 315 South Bradford St., North Andover.

Harpoon Dogtoberfest

Dog lovers, grab your furry friend and head to Harpoon’s Dogtoberfest for a fun-run/walk, costume contest, food trucks, Harpoon and UFO beers, and more. Tickets are $15-$30. 10:30 a.m. to 4 p.m., Harpoon Brewery, 306 Northern Ave., Boston.

King Richard’s Faire

New England's largest and longest running Renaissance Festival is back for another season filled with entertainment, rides, games and more. Open weekends through Columbus Day. 10:30 a.m. to 6 p.m., 235 Main St., Carver.

Salem Food Truck Festival

The Salem Food Truck Festival returns with 45 of the areas top food trucks. From grilled cheese to whoopie pies, there’s something for everyone. 11 a.m. to 6 p.m., Salem Common, Salem, MA.

Allston Village Street Fair

Enjoy Boston’s thisural festival complete with live music, food court, amusement area and more. Noon to 6 p.m., Harvard Avenue, Allston.

Bites + Brews with Remnant Brewing

Out and about today? Stop by the Remnant Brewing pop-up on the plaza alongside rotating BPM food vendors at the Boston Public Market. Noon to 8 p.m., Boston Public Market, 100 Hanover St., Boston.

Contact Us