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Fall Fun and Spooky Spectaculars North of Boston!

August 31, 2023

From apple picking to hayrides, stunning foliage to outdoor excursions, shellfish celebrations and Haunted Happenings all October-long in the Halloween capital of the world, North of Boston is your go-to destination for fall fun and spooky spectaculars!


Kick off the season with Essex Heritage’s Trails & Sails featuring 10 days of 150+ free events including historic walking tours and home tours, art exhibits, schooner sails, guided hikes, and excursions on the water September 15-24.


The Trustees offer outdoor and educational programming through their Crane Outdoors series, including kayak excursions, intimate island tours, full moon dune hikes and more. Get outside and explore all of the natural beauty that North of Boston has to offer.


The Topsfield Fair – America’s oldest agricultural fair – returns September 29-October 9 for animal encounters, fruit and vegetable competitions, flower displays, unique shopping, carnival rides, live music, and of course – fair food! The fair begins with the 39th annual All New England Giant Pumpkin Weigh Off which has received world-wide recognition.


Fall festivals invite foodies and craft beer connoisseurs to taste and sip all autumn long. The Salem Food Truck Festival returns September 23-24 with some of the area’s most popular food trucks and craft brewers. Newburyport’s Oysterfest in the Port on September 30 will bring together oyster farms from across New England to highlight delicious local oysters. The event will feature a “learn to shuck” station, live music and local brews. The 39th Annual Essex Clam Fest on October 21 is an wonderful opportunity to sample the best clam chowders the region has to offer which includes the famous Woodman’s of Essex –  inventor of the fried clam.


Edward Hopper and Cape Ann: Illuminating an American Landscape is on display at the Cape Ann Museum in Gloucester now through October 16. Art enthusiasts won’t want to miss this exciting exhibit from one of the painting world’s greatest.

Head to one of the area’s many agricultural farms and treat yourself to house-made apple cider donuts. Ipswich is home to Appleton Farms, Marini Farm, and Russell Orchards where you can visit with pigs, chickens and sheep, taste fruit wine and cider, or bring home a delicious pie from an onsite bakery. Indulge in hive-fresh honey from Smolak Farms in North Andover or pick-your-own apples at Cider Hill Farm – which boasts the title of Best Apple Picking Spot in the United States from Yelp.

The fun doesn’t stop in October as 31 days of parades, costume contests, jack-o-lanterns and festivals take over downtown Salem during their signature Haunted Happenings event series.  Put on your favorite costume and take a tour of the iconic Salem Witch Museum, or dine on fresh off the boat seafood at one of the many waterfront restaurants. Tour a haunted house, attend a spooky séance, or dance the night away at the Vampire Ball. Each year, Salem welcomes more than half a million people for a month steeped in history, haunts, and a bit of magic.

Photo Credits: Hero image – Courtesy of Cider Hill Farm, Amesbury;  Apple Cider Donuts – Courtesy of Cider Hill Farm, Amesbury; Horses Courtesy of Topsfield Fair; Salem Witch Museum Courtesy of John Andrews / Creative Collective. 

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