September Happenings North of Boston

September Happenings North of Boston

August 30, 2023

As talk of cider donuts and corn mazes fill the air we’re still hanging onto the summer fun! The season doesn’t officially end until September 23 and there are still several weeks of farmers markets, outdoor concerts, and seasonal celebrations to enjoy! But we’d by lying if we said we weren’t looking forward to cozier nights and farm fall fun!

As we usher in September we’re looking forward to the Gloucester Schooner Festival, Cider Hill Farm’s Country Fair, the Salem Literary Festival, the Rockport Celtic Festival, and more!

Aug 31 – Sept. 3: 39th Annual Gloucester Schooner Festival

Welcome to the 39th annual Gloucester Schooner Festival! This year, the festival starts Thursday, August 31st, 2023 and concludes with the schooner race on Sunday, September 3rd, 2023.  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 we hope you will join in the festivities!

Sept 1: Main Street Gloucester Block Party

Join the Greater Cape Ann Chamber and the City of Gloucester for the last of the three summer block parties on Friday, September 1st from 6 to 10 PM to kick off Labor Day weekend. Featured performer Cate Great will delight the young and old alike with her balancing and juggling skills. Slyde, the NE Revolution mascot, face painting, Mary Poppins, Captain Jack and Cape Ann Vernal Pond will also be on hand to entertain the kids. Visit with street vendors, retailers, and non-profits,. Enjoy the delicious offerings of numerous food trucks, and dance the night away to music on three different stages. A great start to the “end of summer weekend!”


Sept. 1–24: Tall Tales from Blackburn Tavern, Gloucester Stage Company

In celebration of Gloucester’s 400+ Celebration, Gloucester Stage has commissioned local playwright John Minigan (Sleepy Hollow, Queen of Sad Mischance, Noir Hamlet) to write TALL TALES FROM BLACKBURN TAVERN, based on folklore from Gloucester’s 400-year history. Directed by award-winning director, educator, actor, and producer Bryn Boice, this production runs from September 1 – 24.


Sept. 1-3 The Jump Shot, Windhover Center for the Performing Arts

The Jump Shot is a play with original music by Stephen Shore. Imagine CHEERS meets Chekhov!This is a heartfelt and character-driven portrait of a community. It’s the contemporary tale of a local bar that’s struggling to keep the lights on. In one night, this rollicking ensemble of outcasts comes face-to-face with an event that will change their lives forever. The Jump Shot inspired by plays like Sweat by Lynn Nottage and The Weir by Conor McPherson.

Image by Victoria Blewer

September 2: Red, White & Beauport White Party

Red, White and Beauport is back – this time on the water! Make waves with Beauport Cruiselines for an evening of live DJ music, award-winning cuisine, and a gorgeous display of the fireworks -this adults only White Party is the perfect way to end the summer in style on Labor Day Weekend.


September 2: Boat Parade of Lights, Gloucester

The annual Labor Day Weekend event! Check out a berate of illuminated boats, houses and businesses! The parade starts at Jones Creek on the Annisquam River. Boats wanted!


Sept. 2 & 3: Cider Hill Farm Country Fair

Happy harvest season! Join Cider Hill Farm’s for summer apple picking, hard cider & apple tastings, classic fair foods, fall flower cutting, old time-y games, live music, line dancing, tractor rides & more! Admission is free and includes SO MANY free family-friendly activities.

September 5-10: Salem Lit Fest
The Salem Athenaeum is pleased to announce the fourteenth Salem Literary Festival (aka Salem Lit Fest), happening September 5-10. The majority of this year’s festival will be held in-person in locations around Salem, with a few sessions offered online only. The Lit Fest features more than 40 notable writers from across genres sharing their stories and writing advice with each other and you.


Sept. 9: Organically Good Trio Sunset Music Cruise, Cape Ann Cruises

Cape Ann Cruises Presents an amazing evening with Organically Good Trio aboard the Legendary Wejack Fishing Yacht.  Hop aboard and leave the land behind for one of Boston’s top Reggae lineups and catch the sunset on the water as the ocean and tunes move you.  Full Bar onboard (no BYOB).  This is an intimate music setting on a warm, welcoming, and vibey boat!  Don’t miss out. Get your tickets before they sell out!

Sept. 14-17: Rockport Celtic Festival, Shalin Liu Performance Center

In partnership with Rockport Music, Edinburgh-born harpist/composer Maeve Gilchrist and WGBH’s Brian O’Donovan proudly present the 4th Annual Rockport Celtic Festival celebrating the music of both the Celtic and French diaspora in Eastern Canada. As always, the Festival features a wide and quite extraordinary variety of new and familiar musicians, singers and storytellers.


September 16 & 17: Farm Days, Appleton Farms

Join us for our Annual Fall Celebration at Appleton – Farm Days! Spend the afternoon exploring the farm, listening to music, enjoying great food & beer, hiking our 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, Local Beer Vendors, Live Music, Shop the Farm Store and more!


Sept. 15-24: Trails & Sails – Essex National Heritage Area
Trails & Sails is a full 10-days of 150+ free events across Essex County, and we’re pleased to share a few resources to help you plan your adventure! SEE EMAIL

Sept. 21: 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 by The Chuck Walker Quartet, and feast on a scrumptious buffet by Kitchen to Aisle Caterers. Play games of chance to win prizes! Get fantastic bargains at the silent auction and bid on car-themed items during the live auction!


Sept. 23: Team Haverhill’s River Ruckus

Team Haverhill’s River Ruckus is an annual festival featuring live music, classic cars, Kids Zone, great local foods, and spectacular fireworks over the Merrimack River.

Sept. 23 & 24: Food Truck Festival, Salem

Food Truck Festivals of America returns to Salem with the ultimate food truck experience for a two-day festival that will feature some of the area’s most popular food trucks. The vendors will be dishing out fan favorites as well as dozens of regional and national craft breweries.

Sept. 24: Ani DiFranco, The Cabot

Widely considered a feminist icon, Grammy winner Ani DiFranco is the mother of the DIY movement, being one of the first artists to create her own record label in 1990. While she has been known as the “Little Folksinger,” her music has embraced punk, funk, hip hop, jazz, soul, electronica and even more distant sounds. She will be joined by performer Kristen Ford.

Photo by Anthony Mulcahy


Sept. 28 – October 29: 40th Anniversary celebration of the Cape Ann Artisans
The 40th Anniversary celebration of the Cape Ann Artisans in conjunction with The Gloucester 400™+ Anniversary Celebration is a historical retrospective that will take place September 28 – October 29, 2023, at the Rocky Neck Cultural Center. Former members of the Cape Ann Artisans are invited to participate in the Exhibition.


Sept. 29 – Oct. 9: The Topsfield Fair Returns
The Topsfield Fair, America’s oldest and finest agricultural fair since 1818 returns! The fair features Fiesta Shows’ carnival midway, The Grand Parade, demonstrations (ranging from beekeeping to miniature trains), a Grange Museum, pumpkin weigh-offs, many musical acts and attractions, the 4-H Agricultural/Arts and Crafts exhibits and so much more.


Sept. 29: Rolling Stones Tribute Band, Blue Ocean Music Hall
“Satisfaction/The International Rolling Stones Show” is the international touring tribute show to the World’s Greatest Rock & Roll Band. This Billboard highly rated show is entering their 22nd year in production with over 4000 performances listed to their credit. Their client list includes the nation’s top casinos, performing arts centers, music halls and corporate clients. The likes of Mick Jagger, Keith Richards and cast bring a colorful performance to over 50 years of classic hits.


September 30: 3rd Annual Oysterfest in 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. Paired with craft brews from Riverwalk Brewing and wine by Grand Trunk this event is sure to be the best shucking time ever. Live band, oyster apparel and more!

Sept. 30: 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.

Through October 16: Edward Hopper & Cape Ann, Cape Ann Museum

Now is your chance to see the American artist Edward Hopper’s early works painted on number of visits to Cape Ann at the start of his fame. Though Hopper (1882-1967) had painted for years in relative obscurity, selling only one painting before the age of 40, it was on Cape Ann, with the encouragement of his eventual wife, Josephine “Jo” Nivison, that he began the iconic watercolor landscapes and houses that launched his success.


Through November 5: Gu Wenda: United Nations, Peabody Essex Museum

Gu Wenda is among the most significant artists to emerge from China in the last 50 years. His awe-inspiring installations immerse visitors in a vision of shared humanity, global connectivity, and mass participation. He began as an ink painter, but by 1993 Gu began his united nations series, in which he works with human hair and other bodily materials. In 2000, he debuted his most expansive hair installation to date, united nations: man and space, which recreated the 188 flags of the member states of the United Nations from hair samples sourced from six continents. Using a material viscerally associated with the human body, this dramatic installation makes a powerful statement about what unites us as human beings across borders, racial, and political divides.

Photo by Kathy Tarantola/PEM