Boston

25+ Great Ways to Have Fun This Weekend in and Around Boston

Labor Day weekend is here and summer is winding down. Are you staying in the area and looking for some local fun this weekend? From the 35th Annual Gloucester Schooner Festival to the Boston Jazz Fest, a sunflower festival, a kite festival and everything in between, check out our picks for a weekend of fun for the entire family.

Friday, Aug. 30

Fun Free Fridays

Highland Street Foundation’s Fun Free Fridays offers no-cost admission to some of the most treasured, cultural venues in the state. Today enjoy free admission to: Old Sturbridge Village, the Cape Cod Museum of Natural History, Capron Park Zoo, EcoTarium, Griffin Museum of Photography, Hull Lifesaving Museum, Mass Audubon’s Ipswich River Wildlife Sanctuary, MASS MoCA, Museum of the First Corps of Cadets and the Osterville Historical Museum.

35th Annual Gloucester Schooner Festival

The Gloucester Schooner Festival returns for its 35th year Aug. 30 to Sept. 2. Today enjoy day-long arrivals of participating vessels, followed by the mayor’s reception from 5-7 p.m. and the Gloucester Block Party from 6-10 p.m. downtown on Main Street.

Dine Out Boston

Grab some friends and head out to sample area restaurants for lunch or dinner at special prices Aug. 25-30 during Dine Out Boston (formerly known as Restaurant Week Boston). Find participating restaurants here.

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.

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. 

Boston Jazz Fest

The Boston Jazz Fest returns for its ninth year with its free, ground-breaking festival featuring the most musically diverse array of jazz artists performing at Boston’s Waterfront. 5:30-9:30 p.m., South Boston Maritime Park, Boston.

UB40 Featuring Ali Campbell and Astro & Shaggy 40th Anniversary Tour

UB40 featuring Ali Campbell and Astro & Shaggy 40th Anniversary Tour are coming to the Rockland Trust Bank Pavilion tonight. 6:30 p.m., Rockland Trust Bank Pavilion, 290 Northern Ave., Boston.

Citizens Bank Weekly Cornhole Tournament

The weekly cornhole 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. Enjoy live music from Swipe Right from 6-10 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. 

Boston Harbor Hotel’s Summer in the City Entertainment Series: Movie Fridays “Captain America: The First Avenger”

Friday is movie night during the Boston Harbor Hotel’s Summer in the City concert series. Tonight enjoy “Captain America: The First Avenger” on the big screen for your waterfront entertainment. The movie starts at dusk, Boston Harbor Hotel, 70 Rowes Wharf, 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, plus visitors can view the evenings featured astronomical object through the 11” Schmidt-Cassegrain telescope in the Museum’s Gilliland Observatory. 8:30 p.m., Museum of Science, Boston, Gilliland Observatory, 1 Science Park, Boston.

Saturday, Aug. 31

Sunflower Festival

Labor Day weekend kicks off Lanni Orchards’ 2019 Sunflower Festival. This week-long event features Throughout this week long event, enjoy four acres of beautiful sunflowers in a variety of colors to pick and take photos in. 8 a.m. to 8 p.m. Lanni Orchards, 294 Chase Rd, Rt. 13, Lunenburg.

5th Annual Onset Beach Kite Festival

Join the Onset Bay Association for its 5th Annual Onset Beach Kite Festival. Build-a-kite station for the kids just $5 per kite. Plus, feel free to bring your ow kites. 10 a.m. to 4 p.m., Onset Beach, Onset. 

Maritime Heritage Day

Celebrate Gloucester Schooner Festival's Maritime Heritage Day today. Enjoy traditional crafters, engaging community organizations, expert seafood demonstrations, foot stomping music, schooner sails, and fun-filled family activities on Harbor Loop, along with local fare at their food tents. Schooners will be docked at Maritime Gloucester's Webster Pier with others throughout the city. 10 a.m. to 4 p.m., Maritime Gloucester, 23 Harbor Loop, Gloucester.

Boston Jazz Fest

The Boston Jazz Fest returns for its ninth year with its free, ground-breaking festival featuring the most musically diverse array of jazz artists performing at Boston’s Waterfront. Noon to 9:30 p.m., South Boston Maritime Park, 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. 11 a.m. to 10 p.m., Rose Kennedy Greenway, Boston. 

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 5 p.m., The Rose Fitzgerald Kennedy Greenway, Rings Fountain, Milk Street, 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 5 p.m. and 8 p.m., Charles Playhouse, 74 Warrenton St., Boston. 

Zac Brown Band at Fenway

The Zac Brown Band returns to Fenway for their record 10th and 11th appearance as part of the Plainridge Park Casino Fenway Concert Series tonight. Tickets start at $67.50. 6:30 p.m., Fenway Park, 4 Yawkey Way, Boston.

35th Annual Gloucester Schooner Festival Boat Parade of Lights and Fireworks

The Gloucester Schooner Festival’s Boat Parade of Lights featurings boats traveling on the Annisquam River through the drawbridge and into Gloucester Harbor before ending in Smith’s Cove. is here. All the fun starts at dusk. Following the parade enjoy fireworks over Gloucester Harbor, Gloucester.

Sunday, Sept. 1

Sunflower Festival

Labor Day weekend kicks off Lanni Orchards’ 2019 Sunflower Festival. This week-long event features Throughout this week long event, enjoy four acres of beautiful sunflowers in a variety of colors to pick and take photos in. 8 a.m. to 8 p.m. Lanni Orchards, 294 Chase Rd, Rt. 13, Lunenburg.

35th Annual Gloucester Schooner Festival

The Gloucester Schooner Festival today features: the Parade of Sail from 10:30 a.m. to noon and the Mayor’s Race at 1 p.m., Gloucester.

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.

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. Performances today at 2 p.m. and 5 p.m., Charles Playhouse, 74 Warrenton St., Boston. 

Zac Brown Band at Fenway

The Zac Brown Band returns to Fenway for their record 10th and 11th appearance as part of the Plainridge Park Casino Fenway Concert Series tonight. Tickets start at $67.50. 6:30 p.m., Fenway Park, 4 Yawkey Way, Boston.

Mary J. Blige & Nas

Mary J. Blige and Nas are coming to Mansfield’s Xfinity Center tonight. Tickets start at $30. 8 p.m., Xfinity Center, 885 South Main St., Mansfield.

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