North Shore & Cape Ann Events

Trails & Sails: 16 Days of Exploring Heritage in Essex County

Start date: September 13, 2025 - End date: September 28, 2025
All-day event
Outdoor Activities | Workshops
Explore Essex County’s historic, cultural and natural sites through a series of outdoor activities and indoor tours and events during Trails & Sails: 16 Days of Exploring Heritage in Essex County. Enjoy exploring Cape Ann and other Essex County communities through virtual experiences or small in-person or self-guided tours with safety protocols in place.  For the full calendar of events, go to www.trailsandsails.org.    

The Topsfield Fair

Start date: October 3, 2025 - End date: October 13, 2025
Time: 11:00 am
Festivals | Outdoor Activities

 

The Topsfield Fair - Topsfield MA - Topsfield Fair 2019

 

The Topsfield Fair is known to be “America’s oldest and finest agricultural fair.” The fair features a large carnival midway, demonstrations (ranging from beekeeping to miniature trains), pumpkin weigh-offs, a Grange Museum, musical acts and attractions, the 4-H Agricultural/Arts and Crafts exhibits and more. The carnival midway and food vendors are big draws for the kids small and big.

Check the Topsfield Fair website for schedules and admission prices: https://www.topsfieldfair.org.

Cape Ann Plein Air Festival

Start date: October 4, 2025 - End date: October 12, 2025
All-day event
Art & Exhibitions | Festivals | Outdoor Activities
Cape Ann Plein Air Annual Painting Competition & Festival

For nearly two centuries, Cape Ann has been a destination for painters who prefer to paint out-of-doors, or “en plein air.”  To honor this time-honored tradition, the Cape Ann Plein Air organization hosts a week-long plein-air painting celebration and competition every October. Organized by the Cape Ann Chamber of Commerce, seARTS, and Cape Ann’s leading arts and culture organizations, the communities will see up to 40 of the finest artists in the nation compete for prizes and awards. Learn more.

Where to Stay During the Cape Ann Plein Air Festival

Atlantic Vacation Homes offers a wide variety of vacation rental homes across Cape Ann. We can easily find you a perfect home base from which to enjoy all of the Festival’s events. To book your accommodations, simply view available rentals and enter your desired dates to get a quote. You can also call toll-free at (855) 853-9143 to speak with a Guest Experience Specialist.