While the region remains lively any time of year, we absolutely love autumn here on the North Shore. It’s nice enough to spend whole days outside, but not so hot that you’re sweating; the foliage is in peak bloom; and it’s the best time to enjoy local produce and other fruits of the harvest season. Below you’ll find ten North Shore events this October. Some are at local farms or venues, while others are regional classics that we look forward to year after year, like the Manchester Cardboard Boat Regatta and the Essex ClamFest. Some events are centered around food, some around the outdoors, and others around live music and the arts—and they all revolve around the community. Read on for things to do this October north of Boston.
Smolak Farms Fall Festival Weekends
Oct. 1–29
Every Saturday and Sunday in October, head to Smolak Farms in North Andover for a day of apple picking, live music, lawn games, hay rides, or just hanging out at their outdoor wine and beer bar. They’ll have face painting, crafts, and an animal playground area for the kids, too. Their beer bar features brews from a rotating lineup of local producers like Amesbury’s BareWolf Brewing and Waltham’s Mighty Squirrel. Don’t forget to grab one of Smolak’s cider donuts, some of the best in New England.
smolakfarms.com/2023-fall-festival-weekends
Ghoulish Gardens at Stevens-Coolidge House
Oct. 1–30
For the month of October, the Stevens-Coolidge House in North Andover transforms its grounds into “Ghoulish Gardens.” The 18th century farm turned country estate on 91 sprawling acres is known for its stunningly manicured gardens that bloom throughout spring and summer. But this fall, the gardens have even more to offer—check out their autumn décor, stroll through the Story Walk by the Stevens Memorial Library, and find all the property’s hidden pumpkins.
thetrustees.org/place/stevens-coolidge-house-and-gardens
Salem Haunted Happenings: Grand Parade
Oct. 5
Salem Haunted Happenings returns to Witch City this October, drawing hundreds of thousands of visitors annually to get into the holiday (Halloween) spirit. The season kicks off with the Grand Parade through downtown Salem on Thursday, October 5. Other highlights include Hollow Harvest, a walkthrough Jack-O’-Lantern festival; Mayor’s Night Out on October 6, a night of trick-or-treating for Salem residents; and the Howl-o-ween Pet Parade on Saturday, October 14.
Music and Movies at The Cabot in Beverly
Oct. 5, 21, 26
The Cabot in Beverly hosts some world-class acts this October. On the 5th, actor John Cusack hosts a screening of his 2000 film High Fidelity, followed by a Q&A with the audience. On October 21, Grammy-winning country artist Lyle Lovett and singer-songwriter John Hiatt perform, and on the 26th, Rock & Roll Hall of Fame inductees The Zombies come to town.
Ipswich Illumination
Oct. 5–8
The annual Ipswich Illumination festival returns this October, bringing art exhibits, performances, vendors, and live music to downtown Ipswich. The floating bonfires are the highlight of the weekend—on Friday, October 6, from 6 p.m. to 9 p.m., head to the Riverwalk to see ethereal bonfires float down the Ipswich River. Other happenings that weekend include a poetry showcase on Thursday, October 5, and the Language Lives Weekend Festival Expo, on Saturday and Sunday, where guests can interact with and peruse art from visual artists, designers, writers, and performers.
historicipswich.net/2023/09/21/ipswich-illumination
Manchester-by-the-Sea Cardboard Boat Regatta
Oct. 8
Manchester-by-the-Sea’s annual Cardboard Boat Regatta returns on Sunday, October 8, and it’s just as funny as it sounds—participants build boats out of cardboard and duct tape and see who can paddle the fastest without sinking. It started as a backyard party in Manchester 14 years ago, and now draws spectators and participants from all over the region. There’s no charge to participate, and races take place at the boat launch behind town hall. They’ll give awards for first place, second place, and kids’ first place, along with a few peoples’ choice awards.
mbtscardboardboatregatta.blogspot.com
Appleton Farms Oktoberfest
Oct. 14–15
Practice holding a stein for Oktoberfest at Appleton Farms on October 14 and 15. The weekend-long festival will feature German-inspired food, lawn games, traditional German Hammerschlagen, and live music from oompah band Wunder Kapelle. Local breweries Notch Brewing, Essex County Brewing Company, True North Ale Company, Far From the Tree Cider, and 1634 Meadery will be on site serving up brews, and they’ll have a classic stein-holding competition, too. Timed entry tickets, at either noon or 2:30 p.m., go for $15 per car for members and $20 for nonmembers.
Castle Hill Vintage Car Climb
Oct. 15
The Trustees have partnered with the Vintage Sports Car Club of America for the return of the Vintage Car Climb. Pre-WWII cars will compete in timed races up Castle Hill’s roads and will be displayed in the Great House’s forecourt during the midday break. Guests can also expect live music, food from onsite vendors like Ferreira Foods, Q’s Nuts, Plat Du Jour, and Beefie Boys, and brews from True North Ales, Mill River Winery, and 1634 Meadery in the bootlegger’s garden.
Essex ClamFest
Oct. 21
What better way to enjoy the region’s cuisine than by sampling some of the best seafood around at the 39th annual Essex ClamFest? On Saturday, October 21, head to Shepard Memorial Park in Essex for a day of live music, artisan stands, and food vendors. The highlight of the day is the clam chowder competition—from noon to 3 p.m., local restaurants compete for the title of best clam chowder. The festival is free to enter; there’s a $10 fee to taste the chowders while supplies last.
Sweet Halloween at Cider Hill Farm
Oct. 21–22
On Saturday, October 21, and Sunday, October 22, head to Cider Hill Farm in Amesbury for its Sweet Halloween, a fun (not spooky) celebration geared toward young kids. Make sure you come in costume and ready to trick-or-treat for sweets from the costumed farm staff throughout the property—they’ll even have a costume contest! And as on every autumn weekend at Cider Hill, guests can also expect live music, an outdoor hard cider bar, tractor rides, and apple picking.