Guide to Fall, Fun & Festivals in Milton and Beyond! | The Milton Moms


Barnfest @ Forbes House Museum, Milton

September 20th


Barnfest is back on Friday night this Fall for lots of family fun! Live music by Sam Luke Chase, Mexican from El Barrio Mexican Grill and local beer from Barrel Z.

Cost: $20 for adults, kids are free!



Free Museum Day

Over 40 museums, Boston

September 21st, all day

Over 40 museums in Massachusetts open their doors for free thanks to Smithsonian magazine’s annual Museum Day

Cost: $0



Annual Fall Festive


September 21 @ Weir Farm, Hingham

Celebrate the fall harvest season at this real working farm! Meet the animals, climb a tractor, paint a pumpkin…plus enjoy face painting, live music, food and lots more!

Cost: $25 members/ $30 non members- per family



Dahlia Festival

Cross Street Flower Farm, Norwell


Stroll through the GORGEOUS Dahlias at the farm, enjoy food, live music & tractor rides.

Cost: $0



Milton Porchfest

September 21 in the Columbines area of Milton


This community event unites musicians and neighborhoods and is whole lot of FUN. The majority of bands play within Milton’s columbines neighborhood and porches, driveways, and lawns become their stage!

Cost: $0



Fontbonne Fall Festival

September 28 @ Fonbonne, Milton


This FREE family event is loaded with fun- including bounce houses, touch a truck, face painting, games, food and so much more.

Cost: $0



Rockin’ with Raptors Festival

September 28th @ Boston Nature Center


Hike the trails, see the caterpillars, pet the animals and check out the awesome raptors from the Blue Hills Trailside Museum. Crafts, food, face painting and more!

Cost: $0



Fairbanks Fall Festival & Septemberfest

September 29th @ The Fairbanks House, Dedham


Celebrate Fall at the 4th annual festival for cider, beer, farm animals, craft and many other activities that will have you step back in time

Cost: Free Admission




October 5th @ Boston Nature Center


Celebrate the fall harvest by creating your own carved pumpkin, playing pumpkin games, and enjoying some fine fall food. Learn about the history of pumpkins and the Jack-O-Lantern story. MUST REGISTER IN ADVANCE.

Cost: $8 members/ $10 non members, plus $ per pumpkin



2nd Annual Blue Hills October Fest

October 5th @ the Wakefield Estate, Milton


Neighbors and friends gather to enjoy live music, Octoberfest fare, farm animals and games at this second annual event.

Cost: $20 per ticket, kids are free



Quincy Food Truck & Music Festival

October 5th @ Hancock St, Quincy


Stroll from Quincy High School to Thomas Crane Library and enjoy over 20 food truck vendors! YUM! 5 bands with live entertainment including a kids stage, tons of entertainment and of course, beer and wine.

Cost: $0 entry



Celebrate Milton

October 6th @ Pierce Middle School, Milton

12pm- 4pm

The event will feature local businesses and non-profit organizations, musical entertainment, bounce houses for the kids, and great food!

Cost: $0



Fall Fair & Pumpkin Harvest

October 6th @ Dedham Community House


A free family event loaded with fun! Pony Rides, face painting, crafts, food, pick your own pumpkins and more!

Cost: $0



Needham Harvest Fair

October 6th @ Needham Town Common


This long time event marks the beginning of Fall! Stock up on seasonal produce from the farmers market, check out artisan goods from one of the many vendors and for the kids hop on a trolley ride, enjoy the bounce house, touch a fire truck, get a pumpkin and more!

Cost: $0



Jarvis Harvest

October 12 @ Jarvis Farm, Walpole


Celebrate 5 years of live music, food, a vendor market, petting zoo, inflatable kidz zone and more!

Cost: $10



Wollaston Harvest Festival

October 12th @ Wollaston Elementary School


Great family fun for all! Bouncy houses, silent auction, raffles, food, games, face painting, live entertainment and more. Be a part of this wonderful community event and help support the Wollaston School!



Cranberry Festival

October 12th-13th @ Edaville


Enjoy free admission to Cranberry Festival with purchase of a ticket to Edaville Family theme park. The festival includes vendors, food trucks, entertainment and more all while learning about the cranberry harvest.

Cost: free with ticket purchase to Edaville, OR tickets $10, $5 or free depending on age



10th Annual Harvest Festival

October 19th @ Patriot Place


Meet at Bass Bro Shops and watch as they harvest the cranberries from the cranberry bog! Plus find tons of games, activities, pumpkin painting, sidewalk sales and more.

Cost: $0



Pumpkinfest 2019

October 19th @ New England Base Camp


What can’t you do with a pumpkin? Pumpkin bowling, carving, pumpkin mini golf, catapulting pumpkins and sooooooo much more.

Cost: $30




October 20th @ Boston Nature Center


Celebrate the fall harvest by creating your own carved pumpkin, playing pumpkin games, and enjoying some fine fall food. Learn about the history of pumpkins and the Jack-O-Lantern story. MUST REGISTER IN ADVANCE.

Cost: $8 members/ $10 non members, plus $6 per pumpkin



55th Annual Head of the Charles Regatta

October 19th-20th @ Charles River, Boston


Enjoy the beautiful Fall scenery as you watch men & women race down the Charles River at the world’s largest regatta. Here is how to navigate the crowds and pick a favorite viewing spot. 

Cost: $0



Pumpkin Patch Fair

November 2 @ Quincy Point Congregational Church


Enjoy pumpkins, seasonal food and shop from many local vendors.

Cost: Free



Annual Blue Hills Great Estates Fall Foliage Day

November 2 @ The Eustis Estate, Wakefield Estate and Eleanor Bradley Estate


Visit any of these 3 beautiful sites located within the Blue Hills and participate in seasonal crafts, location tours and live music. Plus you will receive a voucher to come back!

Cost: $5 members, $10 non members ($20 per family), children under 18 are FREE

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