Boston

30+ Great Ways to Have Some Fall Fun This Weekend in and Around Boston

Celebrate the first weekend of fall with lots of great seasonal events you won’t want to miss. Whether you plan to head out to the Big E or take in one of the many festivals happening throughout the weekend, we’ve gathered our picks to help you decide. Check them out:

Friday, Sept. 27

The 143rd Deerfield Fair

New England’s oldest family fair returns for its 143nd year of agricultural family fun. 8 a.m. to 10 p.m., 34 Stage Road, Deerfield, NH. 

The Big E

The Eastern States Exposition returns for more than two weeks of fun for the entire family. New England’s grandest fair draws close to 1.5 million people annually for this can’t-miss event featuring: rides, live performances, games, food, concerts, car shows and so much more. West Springfield. 9 a.m. to 11 p.m., 1305 Memorial Ave., West Springfield.

Trillium Garden on the Greenway

The Trillium Garden returns to the Greenway Wednesday through Sunday. Located at the corner of High Street and Atlantic Avenue, the Trillium Garden on the Greenway is Boston's first fully open-air Beer Garden, featuring draft beers by Trillium Brewing Co. and wine by Westport Rivers Winery. 2-10 p.m., Rose Kennedy Greenway, Boston. 

City Winery on The Greenway

City Winery Boston and the Greenway Conservancy bring City Winery on The Greenway to Dewey Square this summer. This downtown open-air wine garden will feature wine by City Winery Boston, along with beer and cider from Harpoon Brewery. Head down today from 3:30-10 p.m., Dewey Square, Atlantic Ave, Boston. 

Movies on the Harbor: “Forest Gump”

The weather is still warm for outdoor movies and this week's feature is “Forest Gump.” All the fun starts at sunset (7:30 p.m.). The Anchor Boston, 1 Shipyard Park, Charlestown.

Blue Man Group at the Charles Playhouse

Combining music, technology and comedy, Blue Man Group creates a form of entertainment that can’t be defined, but appeals to people of all ages. Described as “innovative,” “energetic” and “wildly entertaining,” the best way to truly understand what Blue Man Group is, is to see the show yourself. Tickets start at $45. 7:30 p.m., Charles Playhouse, 74 Warrenton St., Boston. 

Astronomy After Hours

Enjoy a free night full of astronomy themed fun. Hope for good weather and small telescopes will be available for a hands-on experience. On clear nights the program will take place on the plaza next to the main entrance of the Museum. In the event of rain or threat of thunderstorms, no observing will take place but indoor activities will still be available. 8-10 p.m., Museum of Science, Boston, Gilliland Observatory, 1 Science Park, Boston.

Saturday, Sept. 28

The 143rd Deerfield Fair

New England’s oldest family fair returns for its 143nd year of agricultural family fun. 8 a.m. to 10 p.m., 34 Stage Road, Deerfield, NH

The Big E

The Eastern States Exposition returns for more than two weeks of fun for the entire family. New England’s grandest fair draws close to 1.5 million people annually for this can’t-miss event featuring: rides, live performances, games, food, concerts, car shows and so much more. West Springfield. 9 a.m. to 11 p.m., 1305 Memorial Ave., West Springfield. 

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.

Arcadia Folk Festival 2019

The Second Annual Arcadia Folk Festival, sponsored by Signature Sounds and Mass Audubon will end the year-long celebration of 75 years of the Arcadia Wildlife Sanctuary with dozens of performances you don’t want to miss. 10 a.m. to 6 p.m., Mass Audubon's Arcadia Wildlife Sanctuary, 127 Combs Road, Easthampton. 

Breakheart Reservation Fall Festival

Join DCR and the Friends of Breakheart for pumpkin decorating, big trucks, the DCR mounted unit and fire patrol, stuff-your-own-scarecrow, take-home crafts, and more at Breakheart Reservation's annual festival. 10 a.m. to 1 p.m., Breakheart Reservation, Saugus. 

21st Annual North Quabbin Garlic and Arts Festival

There is something for everyone at this family-friendly fall event celebrating North Quabbin residents whose livelihoods are connected to the land and the arts. With an emphasis on homegrown and high quality, the festival promises to be engaging, fun and educational. 10 a.m. to 5 p.m., Forster's Farm, 60 Chestnut Hill Road, Orange.

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. 10:30 a.m. to 6 p.m., 235 Main St., Carver.

Salem Food Truck & Craft Beer Festival

Food Truck Festivals of America is coming to the Salem Common and is expected to feature some of the area’s most popular food truck along with dozens of regional and national craft breweries. 11 a.m. to 6 p.m., N. Washington Square, Salem. 

Greenway Open Market

The Greenway Open Market is back for another season featuring area artists, crafters and independent designers. Explore the parks, stroll tree-lined promenades, take in the city sights, soak up the sunshine, play in the Rings Fountain, grab a bite to eat at a food truck, and shop at this original Boston experience. 11 a.m. to 6 p.m., The Rose Fitzgerald Kennedy Greenway, Rings Fountain, Milk Street, Boston. 

Wachusett Mountain Great New England BBQFest

If you’re a BBQ fan, you don’t want to miss the 10th Annual Wachusett Mountain Great New England BBQFest featuring some of the finest he finest area vendors, along with live music, a craft fair and farmers' market, contests, cooking demos and more. 11 a.m. to 5 p.m., Wachusett Mountain Ski Area, 499 Mountain Road, Princeton.

Southie Saturday at The Lawn on D

Enjoy great food, drinks and lawn games on the Lawn on D. Plus, from 2-9 p.m., enjoy live music from the Bearly Dead, New England’s favorite Grateful Dead cover band with Lagunitas Brewing Company featuring live beer, fresh music and giveaways. 11 a.m. to 11 p.m., The Lawn on D, 420 D St., Boston. 

Meadow Walk Fall Fest 2019

Enjoy children's activities, lawn games and more at the Meadow Walk Fall Festival. Noon to 4 p.m., 534 Boston Post Road, Sudbury.

Ipswich Oktoberfest

Celebrate Oktoberfest with Ipswich Ale Brewery and its We're shutting down the street in front of our brewery and building an Oktoberfest-style beer garden complete with beer, food, live Oompah music, stein-hoisting and more. Noon to 6 p.m., Ipswich Ale Brewery, 2 Brewery Place, Ipswich.

Pirates and Princesses Day at the Franklin Park Zoo

Meet your favorite princesses, along with Jack and the Pirates of the Rogues’ Armada as they invade the Franklin Park Zoo today. Plus, learn how to to be a pirate, enjoy crafts, special animal encounters and more. 11:30 a.m. to 2:30 p.m., Franklin Park Zoo, 1 Franklin Park Road, Boston. 

City Winery on The Greenway

City Winery Boston and the Greenway Conservancy bring City Winery on The Greenway to Dewey Square this summer. This downtown open-air wine garden will feature wine by City Winery Boston, along with beer and cider from Harpoon Brewery. Head down today from 1-9 p.m., Dewey Square, Atlantic Ave, Boston.

Blue Man Group at the Charles Playhouse

Combining music, technology and comedy, Blue Man Group creates a form of entertainment that can’t be defined, but appeals to people of all ages. Described as “innovative,” “energetic” and “wildly entertaining,” the best way to truly understand what Blue Man Group is, is to see the show yourself. Tickets start at $45. Performances today at 2 p.m., 5 p.m. and 8 p.m., Charles Playhouse, 74 Warrenton St., Boston.

Sunday, Sept. 29

The 143rd Deerfield Fair

New England’s oldest family fair returns for its 143nd year of agricultural family fun. 8 a.m. to 7 p.m., 34 Stage Road, Deerfield, NH.

The Big E

The Eastern States Exposition returns for more than two weeks of fun for the entire family. New England’s grandest fair draws close to 1.5 million people annually for this can’t-miss event featuring: rides, live performances, games, food, concerts, car shows and so much more. West Springfield. 9 a.m. to 10:30 p.m., 1305 Memorial Ave., West Springfield. 

Grotonfest

Enjoy live music and entertainment, food and more than 150 vendors at Groton’s yearly celebration. 9:30 a.m. to 4 p.m., 75 Hollis St., Groton. 

SoWa Open Market

Stop by the award-winning SoWa Open Market and enjoy Boston's largest celebration of local art, food and music. 10 a.m. to 4 p.m., SoWa Boston, 450 Harrison Ave., Boston.

21st Annual North Quabbin Garlic and Arts Festival

There is something for everyone at this family-friendly fall event celebrating North Quabbin residents whose livelihoods are connected to the land and the arts. With an emphasis on homegrown and high quality, the festival promises to be engaging, fun and educational. 10 a.m. to 5 p.m., Forster's Farm, 60 Chestnut Hill Road, Orange.

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. 10:30 a.m. to 6 p.m., 235 Main St., Carver.

Salem Food Truck & Craft Beer Festival

Food Truck Festivals of America is coming to the Salem Common and is expected to feature some of the area’s most popular food truck along with dozens of regional and national craft breweries. 11 a.m. to 6 p.m., N. Washington Square, Salem.

Wachusett Mountain Great New England BBQFest

If you’re a BBQ fan, you don’t want to miss the 10th Annual Wachusett Mountain Great New England BBQFest featuring some of the finest he finest area vendors, along with live music, a craft fair and farmers' market, contests, cooking demos and more. 11 a.m. to 5 p.m., Wachusett Mountain Ski Area, 499 Mountain Road, Princeton. 

City Winery on The Greenway

City Winery Boston and the Greenway Conservancy bring City Winery on The Greenway to Dewey Square this summer. This downtown open-air wine garden will feature wine by City Winery Boston, along with beer and cider from Harpoon Brewery. Head down today from 11 a.m. to 7 p.m., Dewey Square, Atlantic Ave, Boston.

Boston Women's Market

Shop more than 20 Boston Women’s Market makers, entrepreneurs, and artists while enjoying a glass of wine and harbor views. Noon to 6 p.m., The Anchor, 1 Shipyard Park, Charlestown.

Allston Village Street Fair

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

Barktoberfest

Celebrate Barktoberfest with Sam Adams Brewery and their favorite four-legged friends. Meet adoptable dogs from Shultz’s Guest House and $1 from every pint sold will be donated to the shelter. Your dog is also welcome to join you. 2-4 p.m., Sam Adams Brewery, 30 Germania St., Boston.

Blue Man Group at the Charles Playhouse

Combining music, technology and comedy, Blue Man Group creates a form of entertainment that can’t be defined, but appeals to people of all ages. Described as “innovative,” “energetic” and “wildly entertaining,” the best way to truly understand what Blue Man Group is, is to see the show yourself. Tickets start at $45. 5 p.m., Charles Playhouse, 74 Warrenton St., Boston. 

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