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Before you go, be sure to check with local towns and venues for COVID-19 protocols. Looking for things to do in Boston? Check out our list of 36 things to do in Boston this fall.
Gloucester on Cape Ann beckons with its biannual open studios, and some exciting finds lie in store for the curious wanderer. Follow a self-guided tour map Oct. 9-10 between 8 a.m. and 5 p.m. along over a dozen buildings, each marked by a large pink flag outside. Meet several local artists and artisans, among the most accomplished in the area, who will market their work along the stops in town. Original wares sold include pottery, painting, sculpture, mixed media, mosaics, quilting, weaving, sea glass, and fine jewelry art. — Victoria Zhuang
Guests can shop the gorgeous glass pumpkin display at the 10th Annual PumpkinFest and buy one-of-a-kind pumpkins created by local artists. The event will be held outside on the grounds of the Sandwich Glass Museum on October 23 from 10 a.m. to 5 p.m., with a rain date of Oct. 24. Local artists return each year to hand craft unique, limited edition glass pumpkins in classic shades of orange and other colors. The pumpkins come in various sizes and the earliest guests have more options, since they are sold on a first come, first serve basis. Visitors can also watch the museum’s glassblower create pumpkins inside the museum. Check the museum’s COVID-19 protocols before you go. — Camille Bruni
Stein hoisting is a lifestyle for the lager specialists at Jack’s Abby. Their Framingham beer hall offers a portal to Bavaria year-round, but from Oct. 1 to Oct. 3, Jack’s Abby is doubling down on Oktoberfest with a weekend full of exclusive beer releases, festive activities, and German food specials. VIP packages are sold out, but the beer hall is open all weekend with free admission and reservations available. Plan your prost: The weekend schedule features gravity cask tappings; a Saturday keg tossing competition (sign up to test your strength); and a Sunday flower crown crafting session. Can’t make the party in-person? Jack’s Abby has you covered at home, too. With or without any Copper Legend — and seasonal cans of our favorite local Oktoberfest brew are available in most package stores — you can get in the spirit with a few rousing rounds of Kellner, a properly soundtracked, virtual experience where players must keep thirsty beer hall patrons happy by quickly pouring beers. Challenge accepted! — Jacqueline Cain
The Natick Annual Craftacular kicks off on Oct. 7, making it the perfect reason to take PTO on Friday and IPA your way through a long weekend. The event will feature well-known breweries like Night Shift and Jack’s Abby, but also more local spots such as Start Line, Stormalong, and Penny Pinchers, making it stand out among so many other beer festivals happening in October. Maybe you’ll even run into your boss — just smile, wave, and share an awkward “Cheers!” — Joel Ang
The Salem Harvest Fest returns Oct. 16, and this year, it’s bigger and better than ever before. With two sessions and a larger venue, there will be plenty of opportunity to sample a wide selection of beer, wine, mead, and cider from twenty local vendors, including Jack’s Abby, Artifact Cider, and Tozi Wines. There will also be live music from Salem roots band, Wood & Bone, as well as unlimited snacks to keep you satiated. Costumes are entirely optional, but at a Salem fall festival, you may want to think twice about that polo shirt. — Joel Ang
Over a year after the COVID-19 pandemic upended his Mansfield appearance, outlaw country rocker Chris Stapleton finally makes it to Massachusetts on Saturday, Oct. 2 at the Xfinity Center. Stapleton’s bluesy blend of folk-focused country, on full display in last year’s “Starting Over,” harkens back to the genre’s mountain makers — the likes of Willie Nelson, with nodes of Gregg Allman and other too easy to love masters of yesteryear. While concert-goers may find themselves mouthing along, sharing the agony of a most difficult past year in song, Stapleton says he and his writing partner crafted the lyrics before the health crisis took hold. “As you do with songs sometimes, you write ’em and pull it back out and you listen to it, and maybe it means something else in a different time, which is beautiful,” he told NPR in November. “That’s what actually gives it life to me.” And undoubtedly, we can all use a little life now more than ever. — Christopher Gavin
Not many musicians can claim that they’ve written a novel, let alone two. But Josh Ritter has that accomplishment under his name. Ritter has been around for over 20 years, and is known for his Americana folk tunes. He also has ties to Boston: He first decided to pursue music here. In 2006, he won male vocalist of the year at the Boston Music Awards. Ritter’s slate of shows this fall begins with him promoting his new book, “The Great Glorious Goddamn of it All.” He then has solo acoustic shows lined up across the country. He’s to take the stage at the Somerville Theatre on Oct. 7. — Arianna MacNeill
Rockin’ 4 Vets, Alive & Kicking Productions, and gimmeLIVE have partnered to present a series of performances at Saugus’s Kowloon Restaurant called “Home Grown Rock for Boston’s homeless Vets.” In recent weeks, fans have been revved up by former Boston — the band — guitarist Barry Goudreau’s Engine Room and the dynamite double bill of the James Montgomery Band and Barrence Whitfield. The stage will barely have had time to cool down by the time that Jon Butcher and Sal Baglio ascend it on the afternoon of Oct. 9. Not a lot of musicians from the Boston (or any) area can boast of having toured in the 1980s for J. Geils Band, Rush, Def Leppard, Scorpions, and INXS or “everybody from Aerosmith to U2” (including The Beach Boys). However, Butcher and Baglio — respectively — can do just that. To quote Baglio, “I’ve been very, very fortunate, very lucky to have been able to eke out a living doing this … “[J]ust enough to keep me out of the poor house!” –– Blake Maddux
Louisiana-born blues singer and guitarist Robert Finley was 62 years old when he released his debut album in 2016. It bore the appropriate title “Age Don’t Mean A Thing” and won him a fan in Dan Auerbach of the multi-platinum-selling band The Black Keys. Auerbach — who said of Finley, “He’s the greatest living soul singer as far as I’m concerned” — would subsequently produce the 2017 follow-up “Goin’ Platinum!” and this year’s “Sharecropper’s Son.” In between the release of the latter two albums, Finley was a contestant on “America’s Got Talent,” making it all the way to the semifinals. His show at The Porch Southern Fare & Juke Joint in Medford on Oct. 14 will mark his first visit to the Boston area since his 2018 stop at Brighton Music Hall. — Blake Maddux
Once a year during PorchFest, Somerville transforms into one huge concert, with hundreds of musicians performing on porches across the city. While the festival’s original May date was delayed, the show will go on this Saturday. Things will look a bit different this year. Artists on West Somerville porches will play throughout a noon to 2 p.m. window, while those in Central Somerville will perform from 2 p.m. to 4 p.m. and those in East Somerville will take to their instruments from 4 p.m. to 6 p.m. To see a full map of participating porches and the list of the 100+ artists, check out the PorchFest website. — Kevin Slane
Just an hour’s drive west of Boston will take you to this fun-filled corn labyrinth in Sterling owned by the Davis family for generations. The Mega Maze, open weekends Oct. 2-24, sits on eight acres of land and has almost three miles of walking paths. Each year’s maze is a unique design, and this year it’s “Where’s Waldo?” Spend anywhere from 30 minutes to 3+ hours inside solving the puzzle. If you get lost, Maze Masters nearby can guide you along. You can also play games like The Harvest Toss, Trivial Pursuit Scavenger Hunt, CORN-undrums, and more. Scamper across bridges or pose for photos, whatever you’re in the mood for. Visitors can also listen to live music by local bands, drink craft beers and wine, and eat tasty comfort food, including Kansas City BBQ, buffalo cauliflower, and homemade apple cider doughnuts. There’s something for all ages and interest groups here! Just check the weather before you go. — Victoria Zhuang
It feels like Halloween all year in this town, which is filled with establishments that sell kitschy products harkening back to Salem’s colonial-era witch trials. But after a long wait, now it’s actually Halloween here! The town’s annual celebration, known as Haunted Happenings, occurs Oct. 1-31 and events range from tours to the Haunted Biz Baz Street Fair for local shops, to magic shows, ghost tours, and more. This year, visitors can also download the new Salem app for iOS and Android to further inform their travels. Finally, if you want to meet an actual witch this is the place for it. Today, in a complete about-face from the past, Salem proudly calls itself home to Pagan and Witch religious communities who celebrate Samhain to recognize the end of the harvest season. — Victoria Zhuang
Bring the whole family along for this 65th anniversary of a quirky event celebrating local businesses in the Berkshires, a collaboration between 1Berkshire (the county tourism board) and the City of North Adams. This year the signature activity, a parade through downtown Oct. 3 at 1 p.m., invites parade-goers to design floats and costumes illustrating games they played, movies they watched, and take-out they ate during the pandemic. Along the way, visitors will get to meet several local businesses and community groups. The parade will begin on Curran Memorial Highway and wind for 1.2 miles across a gentle path, making it more walkable and accessible than past years’ events. — Victoria Zhuang
The first annual Honk! Festival of Activist Street Bands took place in Somerville’s Davis Square in 2006. Created by members of the Second Line Social Aid & Pleasure Society Brass Band, the free event featured a dozen brass & drum bands from all over the country playing the raucous, celebratory, joyous, jazzy music – mainly instrumental with some vocals thrown in – usually known as the sound of New Orleans. It was such a hit, participating musicians went back home and created Honk! Festivals in their own cities. Now, the Honk! community stretches to London, Rio, and Paris. Though Davis Square has been Honk!’s home over the years, this time it’s spreading out, with 17 different bands – all of them local – playing in a number of different outdoor locations, including Cambridge, Roxbury, and East Boston on Oct. 9. One thing, though, remains the same. It’ll be a loose, freewheeling affair. Cambridge saxophonist Ken Field, who has performed at the fest every year, and is on the organizing committee, said, “There’s very little infrastructure. The band shows up on a street corner, and plays. You don’t need a PA or a stage.” Specific locations and times are still being set. — Ed Symkus
Looking for a reason to head up to Newburyport for the last time before the colder temperatures kick in? Oysterfest in the Port — featuring fresh catch from a wide variety of New England vendors, beer from Riverwalk Brewing, and wine from Joppa Fine Foods — should be all the reason you need. Tickets for this Oct. 2 event, which runs from 1 p.m. to 5 p.m., include a dozen oysters, tastings of caviar and poke, and some oyster “swag” to brag about at your next virtual meeting. Alcoholic beverages must be purchased separately. — Joel Ang
Quincy is home to a number of great Chinese restaurants, as well as some newer spots serving everything from bánh mì to pink cornmeal pancakes with tres leches cream. On Oct. 2 from noon to 6 p.m., there will be even more culinary choices to choose from at the annual food truck festival. Popular food truck vendors will be present, along with beer and wine available for purchase. Bring your own blanket or chair to relax on the Thomas Crane Library Lawn. — Joel Ang
America’s oldest agricultural fair will once again bring live performances, rides, animal shows, parades, a giant pumpkin display, and more to Topsfield Oct. 1-11. Frankie Avalon, 38 Special, Tony Orlando, Phil Vassar, and Katrina Gustafson will perform at this year’s fair. Fairgoers can visit cows and watch milking demonstrations, enter a hay tossing contest, enjoy fair concessions such as fried dough, candy apples, and turkey legs, ride a Ferris wheel, and find out how many hot dogs they can eat in 7 minutes for a prize. Guests can also watch a Demolition Derby and Double Figure “8” Race. A highlight of the fair is the giant pumpkin weigh off. — Camille Bruni
Before the weather turns the corner and every day looks like a sad scene from Manchester by the Sea, head to New Bedford on October 9 for the annual Seaport Chowder Festival. Fall in New England, after all, requires chowder and beer by the ocean in a L.L Bean fleece. Voting runs from noon to 3 p.m., though if you’re chowder-obsessed you can purchase a VIP ticket that grants you 11 a.m. access to the event. Come to think of it, there probably should’ve been more chowder in that movie. Everyone would’ve been at least a little happier. — Joel Ang
Due to pandemic precautions, the annual Nantucket Cranberry Festival will take place throughout the month of October instead of a single day this year. The festival kicks off on October 9 with the first season’s harvest for sale; for the kids who have no idea what to do with cranberries in non jelly-ridged form, there’ll be a live puppet show for entertainment. If you can’t make it to the kick-off, guided walks of the farm — available on select Tuesdays, Thursdays, and Saturdays in October — are open for pre-booking as well. — Joel Ang
If you don’t spend a lot of time in Waltham, then you’d probably be surprised to know that the University of Massachusetts has a College of Agriculture in the city. That’s where the Waltham Fields Community Farm is located, and on Oct. 16 it’s celebrating its 11th annual Farm Day. Most of the activities are geared towards kids — picking carrots, climbing a farm tractor, and petting rabbits, for instance — but do a quick Google search for “fiber rabbit” (they’re so fluffy!) and you’ll probably want to spend a Saturday doing some petting, too. Should you prefer to snack on more than carrots for the day, there will also host a bake sale, with proceeds supporting the mission of the farm. — Joel Ang
A visit to Cape Cod isn’t complete without a cup of clam chowder and a half-dozen oysters on the half-shell, ideally shucked to order alongside a freshly poured draft beer. On Oct. 16, Cape Cod Beer becomes a one-stop shop for these local specialties during Shuck! A Day of Oysters & Beer. The Hyannis brewery’s fourth annual shuckfest goes down with live music all afternoon, including a 2 p.m. headlining set by bluesy groovers Johnny Hoy and the Bluefish. The day is centered on a raw bar stocked with oysters, shrimp, and littleneck clams sourced from seven local shellfish farms; plus New England clam chowder, provided by Barnstable Association for Recreational Shellfishing, and non-seafood sustenance from JP’s Twisted BBQ. And, of course, there will be plenty of house-brewed suds to wash it all down. Food and beer tickets are sold ahead of time and can also be purchased on-site. A portion of each $10 ticket sold supports the Barnstable Clean Water Coalition, whose mission to restore and preserve clean water throughout Barnstable certainly benefits local beer makers and shellfish growers. — Jacqueline Cain
Dress your kids in their favorite Halloween costume and bring them trick-or-treating among the animals at Stone Zoo’s Boo at the Zoo, taking place Oct. 23-24 in Stoneham. Spooky activities include a trick-or-treat trail with lurking animals, mystery animal encounters, a scavenger hunt, games, and costume contests. Zoo educators will discuss creepy creatures, animal enrichment (watch many of the animals receive pumpkins!) and the importance of buying treats made with sustainable palm oil. Guests can snag snack samples from a Sun-Maid booth on Oct. 24. Guests can review Zoo New England’s COVID-19 health & safety information before heading out. — Camille Bruni
The East Cambridge Business Association’s “Smoke This” Rib Fest is switching things up this year, turning the event into a two-week-long barbecue crawl that wraps up on Oct. 10. Your goal between now and then? To try as many rib and barbecue specials that you can at participating restaurants. Order slow roasted pork coppa with a spicy molasses glaze from Loyal Nine, tempura pork ribs with a jalapeño and maple glaze at Puritan & Co., five spice pork ribs served with fries at Shy Bird, and more. — Erin Kuschner
There are some strict ground rules for this Oct. 24 dinner at the Hawthorne Hotel in Salem. Latecomers will be turned away. Silence must be observed throughout the entire evening. No one is permitted to write notes. The meal will be served backwards, with the silverware placed in reversed fashion. The rules are meant to create a welcoming environment for departed loved ones, and participants are encouraged to bring photos and personal mementos as well to help with the summoning. If you’re wondering what one would eat on such an occasion, well, a five-course meal that includes lobster bisque, of course. — Joel Ang
Head to the orchard-dotted hills of Franklin County for the annual CiderDays to mark the end of apple season with fermented fun. This year, a self-guided “cider trail” stops at local growers and hard cider producers from the Quabbin Reservoir to the Berkshires. On Nov. 6 and Nov. 7, Western Mass. venues like New Salem Preserves & Orchard and Artifact Cider Project will have a pick-your-own lineup of cider tastings, tours, demos, and more pandemic-safe activities. Check out the full list of venues online. — Jacqueline Cain
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