Apple Picking! Corn Mazes! Haunted Happenings! Oh, My! What to do North of Boston in October

Apple Picking! Corn Mazes! Haunted Happenings! Oh, My! What to do North of Boston in October

September 27, 2023

It’s fall y’all! Nothing says fall in New England like weekend drives through our quaint seaside towns as the leaves turn and the weather chills, stopping to savor finger-licking good cider donuts and pick your own apples at one of our charming local farms. Fall is here so raise a glass of cider and settle in to learn all that is happening this month in our glorious region!

Where to Experience Farm Fun:



Russell Orchards, Ipswich

Hop a hayride to the apple orchard, snack on cider donuts, and sip on award-winning fruit wines and hard cider at this beloved North Shore farm.



Cider Hill Farm, Amesbury

Pick your own apples at the number 1 apple picking destination in the country according to Yelp! On the weekends enjoy hayrides, a hard cider bar, free live music, and an on-site food truck.



Smolak Farms, North Andover

Make a day of it during one of their Fall Festival Weekends, every weekend through October, featuring their famous apple cider donuts, apple picking, live entertainment, hay rides, crafts, and more!



Marini Farm, Ipswich

Don’t miss their educational and interactive experience featuring 18 stations with the theme of Alice and Wonderland this year! On September 30th enjoy a Brew Your Way Through event in partnership with True North Ale Company or Wine Your Way Out on Sunday, October 8.


Don’t Miss These Exciting Events Happening Across Our Region!



 Through October 31: Hollowed Harvest: Wicked Labyrinth, Salem

Experience Salem’s ONLY Jack-O’-Lantern festival at the Hollowed Harvest: Wicked Labyrinth! Salem’s beloved fall tradition brings hundreds of intricately carved Jack-O’-Lanterns to life in an all-ages walkthrough event. Enjoy hands-on pumpkin carving where you can roll up your sleeves and get into the spirit of Halloween by carving your very own masterpiece!



Sept. 29–Oct. 29: Long Hill’s Halloween on the Hill, Beverly

Long Hill is excited to bring back the annual Halloween on the Hill event! Explore their beautiful property as we transform Long Hill into a celebration of autumn and the Halloween season. As always, there are a few new surprises and of course many more pumpkins this year. Follow our seasonal-themed trail that will feature over 1,000 jack-o’-lanterns, hundreds of mums, elaborate Halloween decorations, light displays, music, and more. This is the perfect Halloween event for the whole family! Advance tickets required.



Sept. 29–Oct. 9: The Topsfield Fair!

Fall farm fun abounds at the Topsfield Fair, going on September 29 through October 9. This quintessential county fair boasts traditional agriculture, big entertainment, rides, games, shopping, and great food… there’s something for everyone! Browse the offerings of hundreds of vendors and be wowed by the talent and showings of the competitors and performers.



Sept. 29: Final Fridays: Fall Fest

It’s The Kick-Off of the Fall Season and Lynn Museum/LynnArts will be hosting a “Fall Fest” as a part of their September installment of Final Fridays! Taking place Friday, September 29th from 6pm – 9pm at Frederick Douglass Park. Final Fridays is a series of FREE arts and culture events used to activate local spaces and elevate community collaboration on the last Friday of every month. “Fall Fest” aims to celebrate the fall season through family-friendly activities, vendors, and breweries!


Sept. 30: ArtOberfest, Salem

This year, along with their annual Artoberfest Exhibition the Salem Arts Association will offer a free, day-long outdoor event featuring live music, performance art, food, and beer. Through November 11 visit Salem Arts annual Artoberfest which explores Salem’s history with Autumn, Halloween, Witchcraft, and the Spirit of the season.


Sept. 30–Oct. 29: Haunted Happenings Marketplace, Salem

This exciting shopping event returns to Salem Common! Enjoy vendors, performances, mural pop-up photo stations, street performers, and more when the Haunted Happenings Marketplace comes to Salem Common every Saturday and Sunday through October 29.


Oct. 5: Annual Salem Chamber of Commerce Haunted Happenings Grand Parade

The Salem Chamber of Commerce cordially invites you to enjoy or participate in the Annual Salem Chamber of Commerce Haunted Happenings Grand Parade on Thursday, October 5. The parade will follow the normal route from Prime Group Shetland Park to Salem Common. This year’s event will feature the theme “Myths & Legends”. This time-honored kick off the Halloween season is full of color, pageantry, music and the enthusiasm of thousands of Salem’s students from kindergarten to college and their local business owners.



Oct. 7 & 8: Cape Ann Artisan Fall Tour

This year marks the 40th year for the Cape Ann Artisan Tour as the oldest “open studios” in the country. The Fall Tour will be held Saturday and Sunday, October 7 and 8th – 10 am to 5 pm. The tour itself includes 17 current members of the Cape Ann Artisans located throughout Gloucester and Rockport. For those that would like to sample the work all in one place, before and after the tour, the Artisans offer select curated work at The Cultural Center at Rocky Neck for a special 40th year exhibition.


Oct. 7: North Shore Roast Beef & Beer Festival

Bent Water Brewing in Lynn is teaming up with some delicious North Shore restaurants and breweries for the second North Shore Roast Beef & Beer Festival. Sip on brews from Bent Water Brewing, Coastal Mass Brewing, Rockport Brewing Company, and Notch Brewing, and savor roast beef sandwiches from some of the best in the business on the North Shore.


Oct. 9–14: Indigenous Heritage Film Festival, Gloucester

Gloucester 400+ will be hosting an inclusive educational film festival that honors Indigenous Peoples’ experiences and contributions on and beyond Cape Ann. These free screenings are being held at various venues throughout the City. The Indigenous Heritage Film Festival is a week-long celebration of the Indigenous history and cultural contributions of Cape Ann’s earliest inhabitants.



Oct. 9–14: Newburyport Fall Fest, Downtown Newburyport

Join the Greater Newburyport Chamber of Commerce for their Fall Fest and FALL in LOVE with Newburyport. Be entertained by local bands, feast on the offerings of food trucks, sip on seasonal libations and shop from local artisans and crafters in downtown Newburyport on Saturday and Sunday from 10 am to 6 pm.



Oct. 14: Howl-o-ween Pet Parade, Derby Wharf, Salem

Salem is going to the dogs (and cats and lizards and bunnies), and we couldn’t be happier about it! Salem Main Streets hosts the return of the beloved annual Howl-o-ween Pet Parade with the usual fun, costumes, and contest with prizes.



Oct. 15–29: Tales of the Macabre, House of Seven Gables, Salem

This October, the House of Seven Gables is excited to offer three different theatrical experiences! From October 15th to 29th, they invite you to enjoy Tales of the Macabre. ​Tales of the Macabre is a one-woman show performed by The Petticoat Pages. From Poe to Irving with a dash of Dickens, Jennifer whips up a maudlin Victorian performance.



Oct. 21 & 22: Sweet Halloween, Cider Hill Farm

Join Cider Hill Farm for Sweet Halloween, a not-so-spooky, trick-or-treating experience brimming with sweet treats and boo-tiful fall foliage! Children can wear their favorite costumes and trick or treat around the farm. The day includes tractor rides, costume competition, cold brew and hot cider bar, food truck, live music, and more!


Oct. 22: Chamber Music Society of Lincoln Center, Rockport Music

A supreme virtuoso pianist and composer, Sergei Rachmaninov stole the hearts of listeners worldwide with achingly beautiful melodies and alluring harmonies. This Chamber Music Society of Lincoln Center concert brings Rockport’s favorite—pianist Gilles Vonsattel—to the stage with a star-studded ensemble.


Oct. 23: History & Cultures of the Great Salt March, The Governor’s Academy, Byfield

Join the Museum of Old Newbury for a day-long conference to learn about the rich heritage and diverse cultures of Essex County’s Great Marsh. Expert speakers will cover topics ranging from the indigenous peoples who lived in the area, the impact of European settlement on the development of the Great Marsh, the art that this beautiful place inspired, and the challenges facing the region’s most captivating natural landscape today.



Oct. 28: Moonrise Party, Emerson Inn, Rockport

Join the Emerson Inn for dinner, drinks, and music; a wonderful evening waiting for the moon to rise over the Atlantic at their Moonrise Party! Start the evening at 5 pm with their fisherman friend Sasquatch singing his original songs about the days on the water. Then THE JANTELLE’S will be rocking the Veranda with 50s and 60s music plus the Cape Ann Makers Market will be on our lawn with 15 amazing vendors!


Oct. 28: HOLLYWOOD HORROR NIGHT, Salem Waterfront Hotel & Suites

Wicked Night on The Wharf Presents: HOLLYWOOD HORROR NIGHT at the Salem Waterfront Hotel & Suites! Step onto the blood-red carpet, Rise out of the graves and join Hollywood’s finest for one night only and a chance to win an Oscar for Best Costume of the Night! Wicked Night on The Wharf Presents Hollywood Horror Night and encourages guests to dress up as their favorite Hollywood Star Dead or Alive!



Oct. 28: Rockin’ Halloween Costume Ball with WildFire, Blue Ocean Music Hall

Experience the most fun Halloween party on the seacoast. Celebrate Halloween at the Blue Ocean Music Hall’s Rockin’ Halloween Dance Party with entertainment from the band Wildfire. Enter through the haunted maze of illuminated pumpkins, witch hat luminaries, floating candles, giant spiders, smoking cauldrons, tabletop candlelit eyeball jars, cool stage lighting scenes and more! Come dressed to impress for your chance to win part of the $1000 in cash prizes that will be awarded for best costume. 21+.

Looking for more ways to celebrate the Spooky Season? Be sure to check out all the Haunted Happenings taking place in Salem at Remember, you can always find a round-up of fun and festive events North of Boston on our online events calendar.

Photo credits: Russell Orchards courtesy Russell Orchards; Cider Hill Farm courtesy Cider Hill Farm; Smolak Farms courtesy Smolak Farms; Marini Farms courtesy Marini Farms, Topsfield Fair courtesy Topsfield Fair; ArtOberfest courtesy Salem Arts Association; Haunted Happenings Marketplace courtesy Haunted Happenings/Creative Collective; Haunted Happenings Grand Parade by Creative Collective; Howl-o-ween Pet Parade courtesy Salem Main Streets; Chamber Music Society courtesy Rockport Music.