Category Archives: Events

63rd Annual Gloucester Sidewalk Bazaar

The 63rd annual Gloucester Sidewalk Bazaar is scheduled to take place this weekend, Thursday through Saturday, August 4th to 6th on Main Street in downtown Gloucester.

This year’s event features over 55 participating merchants, vendors and non-profits. The Sidewalk Bazaar is the largest Gloucester marketplace event of the year, known for days of bargains, music, food, and discounts, along with new and exciting merchandise by a variety of merchants and vendors alike.

Entertainment will be provided all 3 days by a selection of musicians. Acoustic musician A.J. Fronce will be located at the Parson Street Stage. Arnie Rosen, musician, and vocalist Deanna Brunetti will perform at the Cape Ann Savings Pocket Park. The Cape Ann Vernal Pond Team will be on hand to show and tell about their gallery of snakes. Cape Ann Bible Church will be with us again, providing games for young children.  

For the ultimate “taste of Gloucester” experience, Nana’s Fried Dough will be on deck this year, along with all the wonderful Gloucester Main Street restaurants.

Enjoy the waterfront and experience the 2022 Gloucester Sidewalk Bazaar.

Cape Ann Plein Air Festival Week 2021!

Cape Ann Plein Air Festival Week 2021 is underway! 35 artists from across the country have landed here in town and will begin painting.
Find out why artists from around the world are drawn to America’s oldest sea port. Stroll through artist galleries and studios nestled on the Atlantic. Grab lunch on the water overlooking a working fishing harbor. Experience arts and culture at one of the world-class museums, theater, or heritage center. Venues offer a calendar of special events and daytime galleries perfect for a casual visit or an overnight stay.
Many paintings will be available for sale during the full duration of the competition and festival. Selected works will be shown and available for sale during the Gala Reception and Awards Presentation, at the conclusion of the competition. This is your chance to purchase works by some of the top names in contemporary painting.
For more information visit:

Attend a Performance or Festival

A visit to Cape Ann is only complete by experiencing live music at a local restaurant or nightspot; watching a dance performance, concert or play; attending one of Cape Ann’s renowned community events and festivals, including St. Peter’s Fiesta, Waterfront and schooner festivals in Gloucester, the Essex Clamfest, Harvest Festival in Rockport, Manchester’s Festival by the Sea and, of course, the winter holidays-Celebrated in all four communities, each with their own special flourishes. Whether it’s the height of summer or the heart of winter, there is always a performance, event, or festival happening. Visit the community calendar of events at

Our Final Takeout Today Featured Member: Mile Marker One Restaurant & Bar  

This week marks our final week of Takeout Today and we encourage you to visit Mile Marker One at Cape Ann’s Marina Resort in Gloucester. With locally caught seafood, grass-fed beef, and a selection of cocktails, there’s something for everyone. Visit them after Wednesday this week when their Bridge Deck opens. You can dine with them inside or outside at the water’s edge, you can even dock and dine by boat! Breakfast, Lunch, Dinner and Drinks are also available to-go for curbside, dockside or delivery. Follow Mile Marker One on social media to stay up to date with all their activities.

Cape Ann Chamber’s Irish Sweepstakes Event

Join us at the Gloucester House from 5-7 for your chance to walk away as a winner. Buy your tickets and bring your lucky charm because the Cape Ann Chamber of Commerce is giving away $15,000 at their 17th annual event. The sweepstakes offers live Irish music, a 50/50 raffle, a traditional dinner and much more. The tickets are $100 each, grating you and a guest entrance to the event. To purchase your tickets call the Cape Ann Chamber of Commerce at 978-283-1601.

Irish Sweepstakes
Thursday, March 17, 2016
Gloucester House
63 Rodgers Street, Gloucester, MA

Caoe Ann Chamber Irish Sweepstakes

Jesse Cook

Jesse Cook
Friday, March 11, 2016
Shalin Liu Performance Center
37 Main Street

cape ann chamber of commerce and the shalin liu present jesse cook
Constantly searching for new sounds, rhythms, and textures Jesse Cook is coming to the Shalin Liu on March 11 at 8pm. Cook has taken nouveau flamenco to places it has never been. Cook also is known for his genre-bending compositions. Come to the Shalin Liu Performance center in Rockport to see one of the most celebrated instrumentalist on the plant perform. To register for this event go here, you can also purchase your tickets online here

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