Hayrides, hikes, and Halloween—oh, my! Between the North Shore’s long list of fantastic family-run farms, Salem’s Haunted Happenings, and autumn fairs and festivals galore, it’s a little overwhelming to plan your October schedule. We’re here to make it easier. Read on for 25 things to do this October north of Boston—from the yearly classics like the Topsfield Fair to one-time seasonal events you won’t want to miss, including dinners and spooky movie screenings. You’ll also find our top spots to hike, bike, drink beer, and eat cider donuts.
- Check out Salem’s Haunted Happenings
It’s no secret that Witch City comes alive in October—and there’s even more to do in Salem in the fall than you likely realize. You’ll find events every day in October like Hollowed Harvest (a jack-o’-lantern festival), a food court on Salem Common, and shows like Guilty! A Salem Witch Trial. Other highlights? The Salem Night Faire at Pioneer Village, costume balls galore, magic shows, a haunted speakeasy, and an artisan marketplace every weekend.
- Take a hayride
What’s more iconically autumn than taking a hayride? Plenty of North Shore farms offer them this fall, including Connors Farm in Danvers, Brooksby Farm in Peabody, and Cider Hill Farm in Amesbury.
- Go apple picking
While you’re hay-riding, you might as well pick apples! We have some of the most stunning apple orchards in the country for a day of family fun here on the North Shore—some of our favorites are Boston Hill Farm and Smolak Farms, both in North Andover, and Russell Orchards in Ipswich.
- Visit the Topsfield Fair
More than 200 years old and counting, the Topsfield Fair says autumn on the North Shore like nothing else. It runs this year from Oct. 3 to 13, bringing with it all the events you know and love, like carnival rides, food vendors (caramel apples or kettlecorn, anyone?), arts & crafts displays, and agricultural celebrations like sheep-shearing demos, horse-pulling contests, and the All New England Giant Pumpkin Weigh-Off.
- Take a hike
With weather that’s cool but not cold and colorful foliage aplenty, October is one of our favorite hiking months. Some fan-favorite trails north of Boston: the Ipswich River Wildlife Sanctuary in Topsfield, Maudslay State Park in Newburyport, and Bradley Palmer State Park in Essex County.
- Or go for a bike ride
The mild temperatures and fairly dry trails make October one of the best mountain biking months on the North Shore. There are some fantastic trails for biking at Harold Parker State Forest in Andover, Bradley Palmer State Park in Essex County, Ravenswood Park in Gloucester, and Boxford State Park in Boxford.
- Drink at Oktoberfest
While many of the area’s Oktoberfests happen in September (as does the OG in Munich!), you’ll find a few celebrations in the month of October itself. Appleton Farms holds one on Oct. 4 with live music; beer from Notch Brewing, True North Ales, and Rockport Brewing Company; its own wood-fired pizza; and a stein-holding competition. And LongCross Bar + Kitchen in Medford celebrates on Oct. 25 with traditional food, beer, and live music.
- Get spooky at PEM
Salem’s Peabody Essex Museum runs can’t-miss seasonal programming all month long. Their “Sinister Streets” walking tour runs most days and offers access into some of Salem’s most historic buildings, while a drop-in shadow puppet–making activity runs most Saturdays. And on Oct. 16 at 6 p.m. PEM hosts an interactive play called Haunted Histories: Condemned.
- Head to Smolak Farms’ Fall Festival Weekends
Every Saturday and Sunday this month, visit Smolak Farms in North Andover for more than just apple picking. The Fall Festival Weekends include live music, food and drinks, face painting, barnyard animals, and pick-your-own pumpkins and flowers.
- Kayak at Crane Beach
Get out on the water this month—on the first two weekends in October, you’ll find guided kayaking adventures at Crane Beach in Ipswich. Choose between sunset kayaks in the Crane Wildlife Refuge, a paddle down the Castle Neck River, or a Choate Island adventure that includes hiking.
- Catch a Halloween flick at The Cabot
The Cabot in Beverly hosts seasonal movie screenings all month long. Catch Hocus Pocus on Oct. 5, Psycho on Oct. 10, a Frankenstein and Bride of Frankenstein double feature on Oct. 19, and Sinners on Oct. 23.
- Visit Rockport’s Harvestfest
Running from 11 a.m. to 5 p.m. in downtown Rockport on Oct. 18, Harvestfest features live entertainment from local musicians, artisan vendors alongside the already plentiful shopping in the town, food and beer for purchase, an autumn-themed window display contest, kids’ activities like face painting and seasonal crafts, and an apple pie bake-off.
- Explore a corn maze
Marini Farm in Ipswich has a seven-acre corn maze each autumn—and it’s interactive, with clues throughout that help you find your way out. Connors Farm in Danvers has a corn maze, too, that’s open both day and night. During the day it’s their “Bee Happy” corn maze, but at night, it’s part of “Hysteria,” a haunted-fields attraction.
- Visit the CAM Green Campus
Open Wednesdays through Sundays, the Cape Ann Museum‘s newest expansion is its Green Campus. It’s located off Grant Circle and Route 128 in Gloucester and hosts its own exhibits—Hammers on Stone, chronicling Cape Ann’s granite industry, opens on Oct. 11. If you haven’t been to the Green Campus, check it out this month.
- Bird or sketch with Essex County Greenbelt
Check out one of Greenbelt’s nature activities this October. Join the Thursday morning birding club on Oct. 2, second Sunday sketching on Oct. 12, or the family nature series on Oct. 18.
- Shop at a farmers market
The produce season is winding to a close here, but there’s still plenty of fresh, local fruits and veggies to be had at farmers markets, many of which are open until November and beyond. Many are on Saturday mornings throughout the month, including Wakefield, Haverhill, and Marblehead. Swampscott’s is on Sunday mornings, and the Lynn Commons market is on Thursdays.
- Head into Boston
Stroll through Back Bay, shop on Beacon Hill, and enjoy an Italian dinner in the North End—Boston’s greatest hits, surrounded by fall foliage.
- Or head out of town
October is a fantastic weekend getaway month, too. Take advantage of off-season rates at some of our Cape Cod and Islands favorites like Chatham Bars Inn, the Nantucket Inn, or Wequasset Resort. Or head up north to Maine or New Hampshire—check out the Portland Harbor Hotel, Mountain View Grand Resort, or the Lake Estate on Winnisquam.
- Dine at an Appleton Farm Dinner
Appleton Farms in Ipswich hosts intimate Farm Dinners each month: multicourse meals held on the farmhouse patio. For the dinner on Oct. 23, the farm is partnering with Newburyport’s Mandarava for a dinner of organic, plant-based, scratch cooking highlighting Appleton’s own produce.
- Check out Cider Hill Farm’s Sweet Halloween
Cider Hill Farm in Amesbury hosts “Sweet Halloween” this year on Oct. 18, 19, 25, and 26. The family-friendly event includes trick-or-treating and a costume contest—and check out the farm’s hard cider and farm store offerings while you’re at it.
- Watch The Rocky Horror Picture Show
The cultiest cult classic of all time, The Rocky Horror Picture Show plays at small venues across the North Shore this October. Catch it at Cinema Salem on Oct. 11, The Cabot on Oct. 25, or Firehouse Center for the Arts in Newburyport on Oct. 31.
- Chill at a local brewery
For a laid-back weekend afternoon full of fall vibes, head to one of the North Shore’s many breweries. Some of our favorites include Brewery Silvaticus with its European-style beers, Oak & Iron Brewing for its seasonal ales, Notch Brewing with its biergarten right on Salem Harbor, and True North Ale Company for its award-winning brews.
- See an Edgar Allen Poe play
On the last weekend in October, creator and performer Livy Scanlon brings their “Edgar Allen Poe Double Header” to Gloucester Stage Company. An imaginative, one-person show, the program is a retelling of two of Poe’s most famous (and spooky) works—The Tell-Tale Heart and The Cask of Amontillado.
- Eat a cider donut
No autumn is complete without at least one (or maybe a few) cider donuts—and there’s no shortage of farms on the North Shore that make them fresh. For some of the freshest cider donuts north of Boston, check out Cider Hill Farm, Brooksby Farm, Smolak Farms, or Calareso’s Farm Stand.
- Chow down at Clamfest
Ever wanted to rule on which clam chowder is truly the best around? Essex Clamfest is your chance. The daylong festival, this year on Saturday, Oct. 25, at Memorial Park in Essex, is now in its 40th year, and features local artisan vendors, food and beer trucks, live music, and a chowder tasting at noon.