Salem’s September Festivals

Salem, Massachusetts, is a wonderful place to visit throughout the year, but fall may be one of our most magical times here in this historic oceanside city. Salem is most well-known for the Haunted Happenings festival in October, but we are also home to many other festivals throughout the year, including three in September: Trails and Sails, the Salem Food Truck and Craft Beer Festival, and the Salem Lit Fest. 

Let’s head to Salem before the crowds descend in October and enjoy the waterfront, brews and literature while basking in the glow of New England leaves and weather. 

Salem Lit Fest 

Love books, literature and storytelling? Start Autumn off right with Salem’s Lit Fest being held Wednesday, September 3, through Sunday, September 7, 2025. Held in historic venues in and around Salem, Lit Fest unites published authors and book lovers and encourages aspiring writers to practice their craft. 

The festival aims to inspire and promote literacy and a love of reading by fostering connections through the sharing of stories. Explore all of the festival workshops and the comprehensive schedule online to plan your trip.  

Trails & Sails 

This year’s Trails & Sails is celebrating its 24th anniversary on the North Shore and is taking place on Saturday, September 13, through Sunday, September 28. Explore the 16 days of free events for residents and visitors to Essex County. 

This event is a beloved tradition that brings awareness and appreciation for heritage resources around Essex County, which is a federally designated National Heritage Area. Historically, Trails & Sails has focused on outdoor activities, such as guided hikes and water excursions. Over the years, it has expanded to include historic house tours, lectures, community celebrations, special exhibitions, craft demonstrations, and many other diverse activities. 

Salem Food Truck & Craft Beverage Festival

This popular festival is a must for foodies and beer connoisseurs. Join us on Salem Common on Saturday, September 20th and Sunday, September 21st, from 11 am to 6 pm. Choose from dozens of food trucks for your meal or brew. 

Get ready to taste a smorgasbord of cuisine, including mouth-watering dishes from some of the area’s most popular food trucks! Indulge in macaroni and cheese, sushi rolls, bold Venezuelan flavors, and wood-fired pizza. Or enjoy sinking your teeth into a Smashburger with all the toppings! Don’t forget a sweet treat after dinner with Cookie Monstah Ice Cream Sandwiches, Whoopie Pies or chocolate-covered strawberries. Wash it all down with your favorite brew! 

Additionally, if you are in Salem during September and near Derby Square (right off Front Street), explore the weekly Salem Farmer’s Market that dates back to 1634. The Salem Farmers Market features local farms every Thursday from 3 pm to 7 pm.  

There is so much to see and do in Salem during every season. Be sure to stop into Real Pirates Salem, where you can learn all about New England pirates and maritime history. We’d love to see you.