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Trails & Sails | Top September Events in Marblehead, MA

This September, explore Marblehead and our neighboring towns’ cultural and natural sites from your choice of 150+ events over the span of 10 days! Be guided through unique landscapes on land and sea, explore historic properties, and immerse yourselves in educative experiences of all kinds. Find what makes Marblehead and the rest of Essex County unlike anywhere else during Trails & Sails! All Massachusetts events are FREE and located within the 34 cities and towns that make up Essex County, including Marblehead, Salem, Gloucester, and Newburyport. Find a complete list of events here and learn how our Marblehead Bed and Breakfast can make your events that much more enjoyable!

Historic home on the water in Marblehead, MA

Notable Marblehead Events

Saturday, September 21, 2019

9:00 AM – 11:00 AM: Little Harbor & Islands Walk

Sunday, September 22

11:30 AM – 1:00 PM: Architecture & Social History Walking Tour of Downtown Marblehead

1:00 PM – 2:00 PM: Social History & Architecture Tour of the Historic King Hooper Mansion

4:00 PM – 5:30 PM: Little Harbor & Islands Walk

Monday, September 23

1:00 PM – 2:00 PM: Social History & Architecture Tour of the Historic King Hooper Mansion

4:00 PM – 5:00 PM: 375th Anniversary Presentation at Fort Sewall

6:00 PM – 7:30 PM: Evening Stroll – Changes in Marblehead 1700 to 1818 & Beyond

Tuesday, September 24

1:00 PM – 2:00 PM: Social History & Architecture Tour of the Historic King Hooper Mansion

4:00 PM – 5:15 PM: 375th Anniversary Presentation at Fort Sewall

6:00 PM – 7:30 PM: Evening Stroll: Changes in Marblehead 1700 to 1818 & Beyond

couple embracing and looking out onto the ocean

Wednesday, September 25

4:00 PM – 5:15 PM: 375th Anniversary Presentation at Fort Sewall

6:00 PM – 7:30 PM: Evening Stroll: Changes in Marblehead 1700 to 1818 & Beyond

Thursday, September 26

4:00 PM – 5:15 PM: 375th Anniversary Presentation at Fort Sewall

6:00 PM – 7:30 PM: Evening Stroll: Changes in Marblehead 1700 to 1818 & Beyond

Friday, September 27

4:00 PM – 5:15 PM: 375th Anniversary Presentation at Fort Sewall

6:00 PM – 7:30 PM: Evening Stroll: Changes in Marblehead 1700 to 1818 & Beyond

Saturday, September 28

9:00 AM – 11:00 AM: Little Harbor & Islands Walk

10:00 AM – 4:00 PM: Cinders & Suds: Servant Life at the Lee Mansion

1:00 PM – 2:00 PM: Social History & Architecture Tour of the Historic Hooper Mansion

Sunday, September 29

11:30 AM – 1:00 PM: Architecture & Social History Walking Tour of Downtown Marblehead

1:00 PM – 2:00 PM: Social History & Architecture Tour of the Historic Hooper Mansion

4:00 PM – 5:30 PM: Little Harbor & Islands Walk

Room 28 at Harbor Light Inn with queen bed and fireplace

Stay at Harbor Light Inn

For all your lodging needs, the luxury accommodations at Harbor Light Inn are perfect for those seeking the best place to stay in Essex County. A delicious full breakfast is included with your room rate as well as complimentary onsite parking. Our historic boutique hotel has everything you need for a relaxing fall getaway, including an outdoor pool in the middle of a lush private garden, so you can just pack your bags and enjoy the warm days we savor this time of year.

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Staying safe against COVID-19

Our guests and employees safety is our first and foremost concern. We want you to be assured you are traveling to a clean and safe place so please see our site for a few of the changes and safety precautions we have recently implemented. We hope to host you soon!

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