35 Great Ways to Have Fun in and Around Boston This Week

Another week is here and this one is chock-full of great festivals and special events the whole family will enjoy. From the Big E to King Richard’s Faire, fall festivals and more, check out our picks for the week ahead.

Monday, Sept. 16 

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. 

Free Comedy Night at McGreevy’s Boston

Enjoy a free comedy night featuring some of the best stand-up comics in the Northeast at McGreevy’s Boston every Monday and Tuesday. Doors open at 7 p.m., show starts at 8 p.m. and it’s a 21 plus show. McGreevy’s Boston, 911 Boylston St., Boston.

Halfway to St. Patrick's Day At The Lansdowne Pub

St. Patrick’s Day is six months away and the Lansdowne Pub is celebrating with live music, giveaways, food specials and more. 8-11 p.m., Lansdowne Pub, 9 Lansdowne St., Boston.

Cityside Free Comedy Monday Featuring Casey Balsham

Enjoy free comedy every Monday night at Cityside Bar with some of the best stand-up comics working today, along with frequent, surprise guests. Come join in the fun to see comedians who have performed on Conan, Comedy Central, Funny or Die, Sirius XM, HBO and more. Tonight it’s Casey Balsham! (Comedy Central, Not Another True Crime Podcast by Betches). There’s no cover charge, it’s 21 plus and it’s first come, first seated, with standing room available if sold out. Doors open at 8:30 p.m., show starts at 9 p.m. It’s Cityside Bar, 1960 Beacon St., Brighton. 

Tuesday, Sept. 17

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.

Boston Public Market at City Hall Plaza

The Boston Public Market brings area vendors to Boston’s City Hall Plaza every Tuesday and Thursday all summer long. 11:30 a.m. to 6:30 p.m. City Hall Plaza, Boston.

Free Comedy Night at McGreevy’s Boston

Enjoy a free comedy night featuring some of the best stand-up comics in the Northeast at McGreevy’s Boston every Monday and Tuesday. Doors open at 7 p.m., show starts at 8 p.m. and it’s a 21 plus show. McGreevy’s Boston, 911 Boylston St., Boston.

Trivia Tuesdays at Dorchester Brewing Company

On Tuesday nights, head on over to Dorchester Brewing Company for Trivia night by Stump! Test your knowledge and have some fun. 7:30-9:30 p.m., Dorchester Brewing Company, 1250 Massachusetts Ave., Dorchester. 

Wednesday, Sept. 18

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.

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.

Thursday, Sept. 19

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.

Boston Public Market at City Hall Plaza

The Boston Public Market brings area vendors to Boston’s City Hall Plaza every Tuesday and Thursday all summer long. 11:30 a.m. to 6:30 p.m. City Hall Plaza, Boston.

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. 

Thrilling Thursdays at The Lawn on D

Come play at The Lawn on D and enjoy great food, drinks, and lawn games. Plus, enjoy live music from Other than Boston from 5-9 p.m. 3-10 p.m., the Lawn on D, 420 D St., Boston.

ICA Free Thursday Night

Did you know the Institute of Contemporary Art is free for all visitors every Thursday? It sure is. 5-9 p.m., Institute of Contemporary Art, 25 Harbor Shore Drive, Boston.

Friday, Sept. 20

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. 

TGIF at The Lawn on D

Celebrate the end of the week at The Lawn on D. Play, enjoy great food, drinks and lawn games. 7 a.m. to 11 p.m., The Lawn on D, 420 D 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. 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. 21

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.

Boxford Apple Festival

Since the 1960s, the Boxford Historical Society has been transforming the East Village for it’s annual Apple festival. Enjoy artisan vendors, local musicians, apple pie and more. 10 a.m. to 3:30 p.m., Boxford.

Smolak Fall Festival Weekends

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.

Night Shift Brewing Oktoberfest

Celebrate Oktoberfest at Night Shift Brewing’s fourth annual celebration. Featuring NSB’s German inspired beers, the event includes a beer garden, brass bands, food vendors, lawn games and more. 11 a.m. to 11 p.m., Night Shift Brewing, 87 Santilli Highway, Everett.

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.

Lowell Irish Festival

The Lowell Irish Festival is one not to be missed featuring live Irish music from national and local acts, as well as food trucks, craft tents, family activities, Irish heritage events and more. Noon to 8 p.m. Lowell.

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. Noon t0 11 p.m., The Lawn on D, 420 D St., 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.

Fluff Festival

Celebrate the invention of Fluff at the 14th annual Fluff Festival celebrating the102nd anniversary of the invention of Fluff on Saturday, Sept. 21 (rain date is Sept. 22). 3-7 p.m., Union Square, Somerville.

Sunday, Sept. 22 

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.

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. 

Smolak Fall Festival Weekends

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. 

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.

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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