Fall Festivals

Fall Festivals

Just because the summer’s over doesn’t mean you need to lock yourself indoors just yet. Fall in New England is so wonderful. Just the smell in the air, the mix of frost, dried leaves, and wood burning in neighbor’s fireplaces, it’s almost as tantalizing as Thanksgiving dinner. So even though the days are getting shorter, there are still enough daylight hours to get out of the house, enjoy the outdoors, and visit some great New England markets and fairs.

 Freeport Fall Festival, Freeport, Maine

Freeport Fall Festival, Freeport, Maine

Here are some of our personal favorites that we can’t recommend enough:


Jamaica Plain Open Studio

September 22nd and 23rd

Jamaica Plain, Massachusetts

Calling all art lovers: This year is the Jamaica Plain Arts Council’s 25th anniversary, and they’re celebrating with plenty of great offerings this year. They’re opening their doors to welcome people in to check our local artists all over town, who work in all sorts of mediums (ceramics, jewelry, photography, sculpture, painting, textile and fabrics -- you name it, there’ll be an artist that specializes in it).

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Website: jpopenstudios.com

Facebook: JPOpenstudios


The Pro.found Vintage Market

September 22nd–23rd,

Lancaster, Massachusetts

The market is located at Kalon Farm and Winery, on RT 117 in Lancaster, MA and situated on a sprawling scenic landscape. Vendors with a vintage lifestyle look will showcase their products in individual tents for a unique collaborative shopping experience. Also enjoy local food trucks. brew, wine and live music for a festive weekend for the whole family.

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Freeport Fall Festival

October 5th-7th

Freeport, Maine

You don’t really need an excuse to take a drive up north for a visit to Freeport. It’s a beautiful, coastal town with plenty of outlet shopping, restaurants, and it’s home to the L.L. Bean flagship store. But here’s another good reason to make the trip: the Freeport Fall Festival. There’s plenty to do for the entire family: local food trucks with delicious food, yoga for kids, live music, fine art, jewelry, photography, bath and body products, face painting, and a chowdah competition.  

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The Vintage Bazaar

October 6th and 7th

Eliot, Maine

Named one of the top 10 vintage bazaars in the country, the Vintage Bazaar has quarterly events that coincide with each of New England’s seasons, and you won’t want to miss their fall offering. Located at the Cumberland Fairgrounds in Cumberland, Maine, you will find over 175 vendors, live music, vintage camper and truck displays, a vintage carnival for the kids, and plenty of salvaged, vintage goodies, crafts, and artisan artwork ready to be found by you.

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Website: mybazaarlife.com

Instagram: @vintagebazaarneweng




Rockport Harvestfest

October 13th
Rockport, Massachusetts

Okay, so we’re definitely partial to Rockport, but we also know the seasonal foods of fall are some of the best ever, so we love Rockport Harvestfest! You can sample local foods, drink some delicious beer, meet local farmers and chefs, go for a horse drawn hayride, pick up some pumpkins and produce, listen to live music, and yes, there are fun activities for the kids, so be sure to bring them along, too! And don’t forget to visit the local shops downtown, many still open through the Holidays.

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Website: rockportexchange.org/programs-events/harvestfest/

Instagram: @rockportexchange


And Remember, Boston’s Weekly Markets run through October:

SOWA Open Market

Every Sunday, May - October, 10 AM - 4 PM

SoWa Open Market has been a popular weekly event in Boston for over a decade. Known for it's great selection of trendy and hip makers from all over New England, you are sure to discover unique gifts, decor, accessories, apparel, and more. It is also a destination for Food Trucks, a Farmers Market, and local artist studios and stores. Parking lot directly across from market for convenience.

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Greenway Open Market

Every Saturday, and 1st and 3rd Sunday, May — October, 10 AM - 5 PM

This open-air artisan market features talented area artists, crafters, and independent designers, and is close to other Boston attractions like The North End, New England Aquarium, Boston Harbor, and Faneuil Hall Marketplace.

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Shackteau Interiors

Shackteau Interiors

Apple Picking!

Apple Picking!