October Brings History, Harvest, and Happenings North of Boston

October is here, and the North of Boston region is alive with seasonal color, cultural celebrations, and historic traditions. From fall festivals and farm gatherings to museum exhibitions, concerts, and walking tours, there’s something for everyone to enjoy this month. Take a look at the full events calendar and plan your next adventure—whether it’s exploring vibrant foliage, diving into local history, or savoring the flavors of the harvest season, October is the perfect time to experience it all.

Weekends in October: Wicked Awesome Wizard of Oz Themed Corn Maze, Marini Farm, Ipswich

Step into fall magic at Marini Farm in Ipswich, where this year’s corn maze and play area takes inspiration from The Wizard of Oz. Wander through winding paths designed with whimsical twists and turns, and discover themed clues that bring the story to life as you go.

Weekends in October: Fall Festival Weekends, Smolak Farms, North Andover

Every weekend in October, the farm transforms into a vibrant celebration filled with themed weekends, family fun, and plenty of fall traditions. Enjoy three weekends of Halloween Spooktacular happening October 4 & 5, October 12 & 13, and October 18 & 19. On October 25 & 26 the Halloween fun continues with their Trunk & Treat event!

October 1-31: Salem Haunted Happenings
Salem Haunted Happenings is the largest celebration of Halloween in the world! Salem is excited to welcome more than a half-million visitors to the parties, parades, vendor fairs, walking tours, museums, attractions, and special events. Plan ahead, put on your costume, and join us for a month that is steeped in history, haunts, and a bit of magic. Photo by John Andrews / Creative Collective

October 2-12: Guided Tours, Museum of Old Newbury, Newburyport

Our friendly, knowledgeable tour guides share fascinating stories in each of the museum’s period rooms and galleries. You will walk through this Federal-period house, from its 1808 beginning as a ship captain’s home to its ownership by multiple generations of the Cushing family. See parts of the home as it was lived in, as well as galleries featuring maritime trade, the churches of Old Newbury, and art works by Newburyport native Laura Coombs Hills.

October 2, 8, 16, 23: Watercolor Floral & Botanical Painting with Alison Odle, Newburyport Art, Newburyport
In this engaging watercolor class, students of all skill levels will explore the beautiful world of florals and botanicals, unlocking their creative potential through expert guidance and hands-on practice. Whether you’re a complete beginner or an intermediate artist, this class will equip you with the techniques to create stunning watercolor pieces that showcase the elegance and intricacy of nature’s wonders. Throughout the course, you will learn foundational watercolor techniques such as layering, blending, wet-on-wet, and dry-brush work, all while focusing on the delicate details of flowers and plants. You’ll have the opportunity to experiment with color mixing, brushstrokes, and composition, while receiving personalized instruction to help you refine your skills. This class will take place on October 2nd, October 9th, October 16th, and October 23rd.

October 3-12: Navigating Art & Science Exhibit, The Cultural Center at Rocky Neck, Gloucester
Navigating Art & Science featuring eight artists who are deeply involved in scientific inquiry and activism. While local scientists search for ways to help ocean species be more resilient to survive the rapidly changing marine environment, these artists, alert to the predicament, are creating art with urgent messages for stewardship and action.

October 3-13: Topsfield Fair
The Topsfield Fair prides itself on being the quintessential country fair – traditional agriculture, big entertainment, and good food!  Whether you prefer rides, music, entertainment, agriculture, exhibits, food, or shows, the Topsfield Fair has something for you!

October 4: Sixth Annual Fall Fair, Jeremiah Lee Mansion Gardens, Marblehead
Join Discover Marblehead and the Marblehead Museum for the 6th Annual Fall Fair on Saturday, October 4th from 10:00am – 3:00pm. It’s sure to be a fun day in the Lee Mansion Gardens with Bubble Bar Boston serving up awesome drinks, music by Paul Simonelli, Intuitive Card Readings with Creative Spirit, Rule of Thirds Photo Booth, Acorn Gallery Students drawing portraits, and an amazing line-up of artist vendors selling their beautiful work. As always, we will be selling Pumpkin Decorating Kits and donating all the proceeds to Marblehead Food Pantry. This event is rain or shine. Free admission. Come out and get an early start on your holiday shopping. Location: 161 Washington Street, Marblehead, MA.

October 4: Oktoberfest, Appleton Farms, Ipswich
Join Appleton Farms for a spirited afternoon of German-inspired fun! They’ll bring the craft brews, live music, seasonal bites, hayrides, lawn games, kids’ crafts, and autumn cheer…you just pack your crew in the car, grab a blanket or camping chairs, and pick your entry time – noon or 2:30 PM.

October 5: Hocus Pocus w/ Live Commentary, The Cabot, Beverly
“Hocus Pocus” fans will go “amuck” for this unique screening event full of behind the scenes anecdotes! Actors Vinessa Shaw (“Alison”), Omri Katz (“Max”), Larry Bagby (“Ice”), Tobias Jelenik (“Jay”) and Jason Marsden (voice of “Binx”) will be watching along with you and providing live commentary! They will conjure a pre-show Q&A and perhaps a little bit of extra “magic!” Get tickets now “before it’s curtains – they evaporate – cease to exist!”

October 6: Monthly Moonrise Party, Emerson Inn by the Sea, Rockport
Celebrate the rising of the moon, over the Atlantic, with great music, food, and drinks!

October 9: Liberated, Larcom Theatre, Beverly
A cheeky, satirical burlesque revue where sultry jazz meets the art of tease in an intimate setting. Boston’s finest dancers and live jazz musicians strike the perfect balance of cheeky charm and classic cabaret, guiding you through the Boston Tea Party, Stamp Act, Boston Massacre and more—all with a wink to 18th-century colonial intrigue. The night features solo and ensemble dance acts, vocalists, live jazz musicians, and more! This must-see celebration is all about breaking free—from British rule and societal pressures to anything holding you back. Join us for a steamy night of Boston pride, jazz, and, most of all Liberation!!

October 10: Fall Fridays on the Farm, Cider Hill Farm, Amesbury
Kick off each fall weekend with free live music from 2:30-5:30 pm. Enjoy the outdoor hard cider bar (non-alcoholic sparkling cider available) and grab some farm snacks in the farm store. The farm store is open daily until 6 pm. Apple picking open daily through mid to late October! See the music schedule: https://www.ciderhill.com/farm-events/live-music

October 11: Cedric Burnside, Shalin Liu Performance, Rockport
Grammy-winning bluesman Cedric Burnside carries forward the raw, hypnotic sound of Mississippi Hill Country Blues while shaping it for a new generation. The grandson of the legendary R.L. Burnside, Cedric’s music blends tradition with rock, R&B, and soul, delivered with grit and honesty. With his new album Hill Country Love, Burnside proves why he is one of today’s most vital voices in American roots music.

October 12: Newburyport Chowder Fest, Yankee Homecoming, Newburyport
Newburyport restaurants compete for the best chowder award. This one day festival is kid and pet friendly with live music, crafters, beverage garden and of course CHOWDER! chowder tasting runs from 12-4.

October 15: The Common Crow’s 25th Anniversary Ball, The Cut, Gloucester
Come celebrate Common Crow’s 25 anniversary in Crow Style! Creative dress/costume encouraged. Anything goes! Enjoy light fare provided by Talise, desserts from Common Crow and Kim’s Pure Pastry. Cash bar. Open seating. Deb Hardy and Brian King will kick the night off, followed by Joe Wilkins and the Beauport Bluegrass Boys. This will be a night of dancing, and most of all COMMUNITY. All ticket sales for this event will benefit all the good works provided by the North Shore Health Project. Don’t miss out on this once in a lifetime, 25th Anniversary Crow Ball!

October 17: Back to Black Live: Amy Winehouse Tribute, Off Cabot Comedy & Events, Beverly
Join us for a night of soulful melodies and heartfelt lyrics as we pay tribute to the legendary Amy Winehouse. Get ready to be transported back in time to the golden era of jazz and R&B. Immerse yourself in the soul-stirring music of Amy Winehouse, performed by talented musicians who share her passion and artistry. From her iconic hits like “”Rehab”” and “”Back to Black”” to lesser-known gems, expect an evening filled with unforgettable renditions. Whether you’re a die-hard fan or simply appreciate great music, this event promises to be a memorable experience. Gather your friends and come ready to groove to the infectious rhythms and powerful vocals that made Amy Winehouse a true icon. Don’t miss out on this incredible tribute to one of the greatest voices of our time. Mark your calendars and join us for a night of soulful nostalgia at the Back to Black Amy Winehouse Tribute.

October 18: Rockport Harvest Fest, Rockport
The Greater Cape Ann Chamber of Commerce presents Rockport’s Harvest Fest, a cherished community event! We invite you to join us by the shore for a unique blend of fall festivities and coastal charm, where the crisp sea breeze meets the warmth of community spirit. Come enjoy live music, seasonal bites, craft brews, local vendors and family fun while you explore the scenic downtown and immerse yourself in festive seasonal activities. Whether you’re a longtime local or just visiting, this is the perfect way to experience the magic of autumn by the sea. So, grab your sweater and your loved ones, and join us for a day of seaside celebration! *Rain Date Sunday October 19.

October 23: Appleton Farm Dinner: Mandarava, Appleton Farm, Ipswich
Immersive and intimate, our Farm Dinners highlight the work of our farmers directly, with the bounty of each harvest brought to life by visiting local chefs. Dine at twilight on the patio of our historic farmhouse, overlooking the Great Pasture and the rolling organic fields from where your meal was harvested. Appleton Farms is delighted to announce the return of Newburyport’s Mandarava, for our October Farm Dinner. Guests will enjoy a multi-course journey of family style seasonal dishes under the setting sun on our Farmhouse patio. There is no one better suited to showcase Appleton-grown organic produce than the talent behind Mandarava. Pop your favorite bottle of wine and enjoy the last nights that summer has to offer with this special meal. BYOB!

October 25: A Vintage Hallowe’en: Hawthorne Hotel’s Annual Costume Ball, Hawthorne Hotel, Salem
The event, introduced in 1990 and hosted by the Hawthorne team, features a live band (American Midnight), two DJs, interactive experiences, a costume contest, stationed hors d’oeuvres, and cash bars across three floors. Dance, people-watch, take selfies in front of our photo backdrops and enjoy being part of the premier bucket-list Halloween event in New England. Celebrate A Vintage Hallowe’en and pay homage to the hotel’s 100th anniversary with an unforgettable evening of eerie elegance and vintage oddity.

October 25: Essex Clam Fest
The Essex Clam Fest and Arts & Crafts Festival, is held annually in Shepard Memorial Park in Essex. Come experience a great variety of activities, including arts and crafts vendors, chowder tasting competition, live entertainment and plenty of food vendors on-site!

October 30: The Cher Show, North Shore Music Theatre, Beverly
Stars come and go .. but Cher is forever! Experience the dazzling journey of superstar Cher in THE CHER SHOW, a spectacular, high-energy celebration of Cher’s life and a career that has spanned over six decades. This extravagant musical features three powerhouse performers embodying Cher at the different stages of her life and will take your breath away with hundreds of Bob Mackie’s dazzling Tony® Award-winning Broadway costumes. THE CHER SHOW features 35 of Cher’s biggest hits, including “Believe,” “Turn Back Time,” and “Str