Sailing Into September North of Boston

September is upon us, and despite back-to-school season, the North of Boston region is still buzzing with excitement! As the summer sun begins to fade and the nights begin to cool down, our charming coastal towns and historic cities come alive with vibrant events and seasonal traditions.

From harvest fairs and art and literature events to food and drink festivals, there’s something magical about the energy that September brings. As summer lingers and fall whispers the weather is perfect for getting out to explore all the region has to offer. It’s that extra special time of year when you can still enjoy days at the beach or go apple-picking at our local farms. And the sunsets, oh the sunsets! Whether you’re planning a weekend getaway or a day trip, this month is filled with opportunities to explore and experience the beauty and bounty North of Boston!

Read down for a look at our featured events and happening to make the most of this exceptional month. For a full calendar of events visit the event calendar on our website.

Aug. 23–Sept. 8: The Servant of Two Masters by Carlo Goldoni: Lanes Coven Theater Company, Windhover Center for the Performing Arts

The Servant of Two Masters is a commedia-del-arte play, originally written in 1746. We’ll be adapting it, as we do, and you can expect a farce, with mistaken identity, masks, silly power dynamics, and high-energy staging! Directed by Jesse Garlick.

August 29–Sept. 1: Gloucester Schooner Festival, Maritime Gloucester

This year marks the 40th Annual Gloucester Schooner Festival. This capstone to the summer is steeped in history and jam-packed with events and opportunities to get up-close and personal with these beautiful ships. The Gloucester Schooner Festival has become a Labor Day weekend tradition for thousands of people every year and a community-wide celebration of the age of sail in Gloucester Harbor. Every year schooners from all over travel to Gloucester to race and to show off their beauty and grace both under sail and as a dock-side attraction. Photo credit Maritime Gloucester

August 31–Sept. 2: Cider Hill Farm Country Fair

Happy harvest season! Join Cider Hill Farm this Labor Day weekend for apples, peaches, blueberries, and flower picking, hard cider tastings, hayrides, face painting, classic fair foods, fall flower cutting, old-time games, animal meet and greets, and more! Check out the Fair Schedule, with events being added daily. Admission is free, register here.

Sept. 2: Bread & Roses Festival, Lawrence
The annual Bread & Roses Labor Day Festival celebrates Lawrence’s history and diverse cultures through music, theater, dance, and art. The event is meant to recognize, commemorate, inform, and share the labor history and social justice legacy of Lawrence’s 1912 Bread & Roses strike with Lawrence’s present-day residents and people worldwide.

September 4–8: Salem Lit Fest
The Salem Athenaeum is pleased to announce the 15th Salem Literary Festival (aka Salem Lit Fest). Salem Lit Fest brings together authors and readers from around the world to celebrate literature in all its forms. The Lit Fest features dozens of notable writers from across genres sharing their stories and writing advice with each other and you. The 2024 Salem Lit Fest will take place in-person and on Zoom. Check out the schedule of sessions.

Sept. 8: CAMTalk: History Series Granite and the Sea in Cape Ann’s History, Art, and Literature, Cape Ann Museum

Offered in conjunction with the Jonathan Bayliss Society’s conference “Granite and the Sea: Exploring the History, Nature, and Arts of Cape Ann’s Rocky Coast.”  Local historian and author Paul St. Germain will present a series of slides from his book Cape Ann Granite. Rebecca Reynolds will discuss “Granite Appeal: How the Rock of Ages Inspired Artists.” The program will conclude with “‘it is elements men stand in the midst of’: Jonathan Bayliss and Charles Olson,” a talk by Gary Grieve-Carlson. Located at the Cape Ann Museum Auditorium from 2 to 3 pm.

Sept. 10: Author Discussion with Clint Smith, Gloucester Stage Company

Join the Gloucester Reads conversation with Clint Smith as he takes us on a tour across America to reveal the hidden history of slavery while inviting us to experience the healing power of knowledge as he discusses his #1 New York Times Bestseller How the Word is Passed. Gloucester Reads is a book club created for the entire community, with the goal of creating a welcoming Gloucester for everyone!

Sept. 12–15: Rockport Celtic Festival, Shalin Liu Performace Center
The Rockport Celtic Festival, under the direction of Maeve Gilchrist, celebrates new and old music from Scotland to Scandinavia! The Festival features Väsen, Jeremy Kittel, Hannah Read, Liz Carroll, and many more!

Sept. 14: Beauport Cruiselines 10-Year Diamond Anniversary Cruise, Gloucester Harbor
Join Beauport Cruiselines for their 10-Year Diamond Anniversary Cruise! Celebrate and toast to this remarkable milestone – one whole decade of creating unforgettable memories along the Gloucester Harbor. Raise your glasses for a complimentary champagne toast, savor an exquisite selection of hors d’oeuvres, followed by an extravagant dinner buffet. Sip on our seasonal cocktails as you take in the breathtaking views of the Gloucester Harbor and dance the night away to live DJ Entertainment, brought to you by The 617 Event Group!

September 14 & 15: Farm Days, Appleton Farms

Join us for Appleton Farms for their Annual Fall Celebration at Appleton – Farm Days! Spend the afternoon exploring the farm, listening to music, enjoying great food and beer, hiking their trails, entertaining the kids, and more. Games and activities for all ages including face painting, sack races, lawn games, farm demonstrations, self-guided nature walks, children’s craft activities, barnyard animals, meet the machines, farmhouse wood-fired pizza, food trucks, beer vendors, live music, and more!

Sept. 14–29: Trails & Sails, Essex Heritage Area

Discover special places in your backyard during Trails & Sails! Be guided through unique landscapes on land and sea, explore historic properties, and take in cultural experiences of all kinds. Find what makes Essex County like nowhere else. This year, Trails & Sails is a full 16-days of 200+ free events across Essex County, and they’re pleased to share available resources to help you plan your adventures! Be sure to utilize the online schedule of Trails & Sails events which is now live. You can even filter to search by date, community, or theme, and take advantage of 200+ free upcoming events!

Photo credit Essex Heritage

Sept. 21: Team Haverhill’s River Ruckus

Team Haverhill’s River Ruckus is an annual festival featuring live music, classic cars, Kids Zone, live demonstrations, art and history talks, great local foods, and spectacular fireworks over the Merrimack River. Happening at Riverfront Park in Haverhill’s Riverfront Cultural District and Washington Street from 12 to 8:30 pm.

Photo Courtesy Team Haverhill’s River Ruckus

Sept. 21 & 22: Food Truck & Craft Beer Festival, Salem

Food Truck Festivals of America returns to Salem with the ultimate food truck experience for a two-day festival!! Get ready for a feast like no other! Over 40 of the most sought-after local and New England food trucks are gearing up to dish out their mouthwatering specialties, while an incredible selection of local and national craft beers will be on tap to quench your thirst. Prepare to be blown away at the 5th Annual Salem Food Truck & Craft Beer Festival taking place in the vibrant Salem Commons.

Photo credit Food Truck Festivals of America

Sept. 26: Driving Through History, Jazzin’ It Up, Amesbury Carriage Museum

You are invited to a jazz-age fundraiser with a 1920’s / 30’s vibe! Check out vintage vehicles, enjoy early jazz tunes, and feast on a scrumptious buffet. Play games of chance to win prizes! Get fantastic bargains at the silent auction and bid on car-themed items during the auction including rides in antique vehicles! You’ll barely recognize the museum turned into a speakeasy serving beer, wine, and gin cocktail tasters.

Sept. 27: Kanin Wren’s Taylor Swift Experience, Blue Ocean Music Hall

Kanin Wren fronts the most dynamic live Taylor Swift Experience for fans of all ages. Playing all of the greatest hits from You Belong With Me to Midnights, Kanin Wren’s Taylor Swift Experience is packing dance floors and creating timeless once in a lifetime memories. With fun choreography, multiple costume changes, spot on musical delivery, Kanin’s tribute to the genius of Taylor Swift is a must-see act.

Sept. 28: Magical Mystery Doors, The Cabot

Magical Mystery Doors is a Tribute Act that blends and layers the music of three legendary bands to create something new and unique for music fans everywhere. The Beatles, Led Zeppelin, and The Doors. These three iconic groups have changed the face of music as we know it. Patrons attending a Magical Mystery  Doors performance can expect to hear timeless tunes from each of these  historic bands throughout the night.  The songs you know, the songs you love, the songs you sing at the top of your lungs!

Photo credit The Cabot

Sept. 28: Oysterfest in the Port, Newburyport

Oysterfest In The Port hosted by Newburyport FISH will bring together oyster farms and fish vendors from across New England to highlight delicious local seafood. Enjoy oyster tastings, a “learn-to-shuck” station, live band, oyster apparel, and more!  Several oyster-adjacent free tastings will be available. Located at the Tannery Marketplace from 1 to 5 pm.

Sept. 28: Artoberfest, Salem Maritime Historic Site

Join Destination Salem and other local organizations for a FREE, day-long event featuring live music, art, creative activities, food, and beer. This outdoor event will be held on the Salem Maritime Historic Site lawn next to Salem Arts Association. Bring a blanket, get comfy and enjoy a day of live entertainment and art on Derby Street in Salem.

Sept. 28: Opening Celebration: A Narwhal Carnival, Peabody Essex Museum
Join PEM as they celebrate the opening of Narwhal: Revealing an Arctic Legend through an array of programs designed to invoke a sense of wonder! Meet fantastical marionette puppets walking through the galleries and create your own sea creature using recycled materials with a local artist. Plus, enjoy an ocean-themed PEM Pals with them!

Through September 30: Salted Cod Arthouse Artists Showcase, Greater Cape Ann Chamber of Commerce

Six talented artists from the Salted Cod Arthouse, all members of the esteemed Rocky Neck Art Colony, are currently exhibiting their unique interpretations of the theme “Sand and Sea” at the Greater Cape Ann Chamber of Commerce. The exhibition features diverse mediums, including archival prints, watercolors, felt sculptures, mixed media, and oil paintings. Participating artists include Jillian Demeri, Leslie Heffron, Jane Keddy, L. Marie Lamarche, Brian Murphy, and Crissie Murphy. The exhibition runs through September 30, 2024. Visitors can view the artwork at the Greater Cape Ann Chamber of Commerce, located at 24 Harbor Loop, Gloucester, MA. The Chamber is open Monday through Friday, from 9 AM – 5 PM.

Photo credit Rocky Neck Art Colony