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October 2020

Gloucester Stage: Think of Me Tuesday – CANCELLED

October 2 - October 18

Originally slated for 2020, but due to Covid-19 social distancing measures has been moved to the 2021 Season, Think of Me Tuesday will run October 1 through October 17. Gloucester resident and playwright, Ken Riaf, returns with his newest play after the hit world premiere of My Station In Life. Think of Me Tuesday tells the story of a candidate who, after continually failed campaigns, suddenly ends up in the city’s hot seat. Newly minted mayor, Jim ‘Buddy’ Chum is immediately faced with a quixotic challenge bigger than any one man can handle.

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Rockport Farmers Market

October 3 @ 9:00 am - 1:00 pm
|Recurring Event (See all)

An event every week that begins at 9:00 am on Saturday, repeating until October 10, 2020

Harvey Park, Mt Pleasant and Broadway
Rockport, MA 01966 United States
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The Rockport Farmers Market provides fresh surprises with its roster of vendors offering small-batch, locally-produced food at each week’s outdoor market, taking place every Saturday morning in the heart of downtown Rockport from June to October.

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Essex River Race

October 3 @ 10:00 am - 11:30 am
Riversbend Restaurant, 35 Dodge Street
Essex, MA 01929
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The Essex River Race is a 5.5+ mile open water event from the Essex River at Route 133 in Essex, out behind the barrier beaches of Ipswich and back. Participants row or paddle small boats through one of the most scenic tidal areas in New England. Occasionally the water can be very rough, with strong winds and currents. As with all on-water activities in such conditions, safety should be the first concern of all participants and organizers. The orderly, safe…

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Beauport Cruiselines Summer Dinner Cruise

October 3 @ 6:30 pm - 9:00 pm
|Recurring Event (See all)

An event every week that begins at 6:30 pm on Saturday, repeating until October 31, 2020

Beauport Cruiselines, Cruise Port Gloucester
Gloucester, MA 01930 United States
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Welcome aboard Beauport Cruiselines, where you’ll cruise the night away on beautiful Cape Ann this fall! Every Saturday through the end of October, join them for weekly sunset dinner cruises sailing around Gloucester Harbor.

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Cape Ann Farmers Market Drive Thru/Pre-Order market

October 8 @ 3:00 pm - 6:30 pm
|Recurring Event (See all)

An event every week that begins at 3:00 pm on Thursday, repeating until October 8, 2020

O’Maley Innovation Middle School, 32 Cherry Street
Gloucester, MA 01930 United States
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Free

The 2020 Cape Ann Farmers Market has moved to the O'Maley Innovation School for their Drive Thru/Pre-Order market featuring 4 local farms and 2 bakeries. 

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Rockport Farmers Market

October 10 @ 9:00 am - 1:00 pm
|Recurring Event (See all)

An event every week that begins at 9:00 am on Saturday, repeating until October 10, 2020

Harvey Park, Mt Pleasant and Broadway
Rockport, MA 01966 United States
+ Google Map

The Rockport Farmers Market provides fresh surprises with its roster of vendors offering small-batch, locally-produced food at each week’s outdoor market, taking place every Saturday morning in the heart of downtown Rockport from June to October.

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Annisquam Arts & Crafts Show

October 10 @ 10:00 am - October 12 @ 5:00 pm
Annisquam Village Hall, 36 Leonard St
Gloucester, MA 01930 United States

Discover a unique shopping experience at the annual Annisquam Arts & Crafts Show, taking place over Columbus Day Weekend. Over 35 local artisans will display their crafts and talents at Annisquam's historic Village Hall offering handcrafted, one-of-a-kind goods for sale. You may just find the perfect gift ideas for the holidays. Admission is free on Saturday and Sunday.

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Cape Ann Artisans Fall Studio Tour 2018 | Discover Gloucester, MA

Cape Ann Artisans Fall Tour

October 10 @ 10:00 am - October 12 @ 5:00 pm
Cape Ann Artisans, Various
Gloucester, Rockport,
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The Cape Ann Artisans Fall Tour will take place over Columbus Day Weekend, October 10 through October 12. The studios are open 10:00 am – 5:00 pm. Cape Ann Artisans are part of a vibrant arts community, located along the scenic North Shore of Massachusetts. The Tour is self-guided of artists’ studios in Gloucester and Rockport. Both areas are also home to three important Massachusetts designated Cultural Districts – downtown Gloucester, downtown Rockport, and Rocky Neck.   Discover and explore…

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Beauport Cruiselines Summer Dinner Cruise

October 10 @ 6:30 pm - 9:00 pm
|Recurring Event (See all)

An event every week that begins at 6:30 pm on Saturday, repeating until October 31, 2020

Beauport Cruiselines, Cruise Port Gloucester
Gloucester, MA 01930 United States
+ Google Map

Welcome aboard Beauport Cruiselines, where you’ll cruise the night away on beautiful Cape Ann this fall! Every Saturday through the end of October, join them for weekly sunset dinner cruises sailing around Gloucester Harbor.

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Cape Ann Plein Air

Cape Ann Plein Air Competition & Festival

October 11 @ 10:00 am - October 17 @ 5:00 pm
North Shore Arts Association, 11 Pirates Lane
Gloucester, MA 01930 United States

Join America’s top painters at the premier New England plein air competition. The Cape Ann Plein Air competition will be held October 11-17, 2020. This celebration of 'plein air' painting includes events throughout the week, including a Quick-Draw competition, Artists Demos, and Collector's preview, followed by our Gala & Art Sale.

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