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May 2020


Trading Main Street Raffle

May 1, 2020 - June 30, 2020

Trading Main Streets Raffle Tickets are NOW AVAILABLE! Gloucester Main Street Association (GMSA) hopes that you and your family are well. We know that these uncertain times are stressful on all. Your local non-profit organization, GMSA is looking ahead to better times. What better way to celebrate the end of the COVID-19 than to get out and enjoy a weekend getaway for two in  Fall 2020 or Spring 2021! Two designated Virginia Main Street communities, Gloucester Main Street and Culpeper…

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October 2020



October 25, 2020 @ 1:00 pm - 2:30 pm
Gloucester Arts On Main, 6580-B Main Street
Gloucester, VA 23061 United States

Join Artist in Residence Michael Rosato, who recently completed the newest Cook Foundation mural on Main Street, for a muralist talk on "The Transformative Power of Public Art." This free event will take place at Arts on Main Sunday, October 25, 2020 from 1 to 2:30 p.m. Rosato has created murals in 22 states in the past 27 years. Viewable from Main Street and Rt. 14, his most recent creation celebrates T.C. Walker and brings to life his impressive life story.…

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TC Walker Mural Dedication and Celebration

October 25, 2020 @ 3:00 pm - 5:00 pm
TC Walker Mural, 6769 Main Street
Gloucester, 23061 United States

Join The Cook Foundation Sunday, October 25, 2020 from 3 to 5 p.m. on Gloucester Main Street for a dedication and celebration of the recently completed mural honoring the life and legacy of TC Walker. Commissioned by The Cook Foundation and painted by Michael Rosato, the mural tells the story of TC Walker himself and highlights the impact he had not just on the Gloucester community, but also the nation. A short program will start at 3:15 p.m. and feature…

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February 2021


Kelsick Presents GloBrewCo Dinner

February 14 @ 5:00 pm - 7:00 pm
Kelsick Specialty Market, 6632 Main Street
Gloucester, VA 23061 United States

Still looking for something FUN  for Valentines? We have a great suggestion on how to keep it local and tasty! Kelsick Specialty Market and Gloucester Brewing Company have paired together to ensure a delicious meal with yummy brew! The event takes place at Kelsick 5p-7p on Sunday, February 14. The special menu is as follows: 1st- Stout battered oysters          Pickled veg          Sriracha aioli 2nd- Grilled smoked brats            Bacon-Corn Hoppin John  …

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Love Your Main Street Treasure Hunt

February 27 @ 11:00 am - 12:30 pm
Gloucester Brewing Company, 6778 Main Street
Gloucester, Virginia 23061

Who doesn't LOVE a treasure hunt??? Especially when EVERY team WINS and no diggin' is involved.....just make sure to wear comfy shoes and be ready to follow the clues!!!!! Don't delay and register today--limited spots available. Over $500 worth of prizes, some will win a little and some will win a lot! Each team will receive a goodie bag full of LOVE--Main Street Style! (includes 2 Gloucester Brewing Company beer tickets). Every team will also be entered to win a gift…

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March 2021

Support by shopping with us an YOU could win either $25 or $100 gift certificate  It's simple: Post a pic of you making your purchase at one of our Main Street stores/restaurants (you at the register with your cashier, include your receipt or shopping bag) and make sure to include the hashtag #GloucesterVillage FOUR winners will be randomly selected to each win a $25 gift certificate If you shop (and post) at 3 or more Main Street businesses, you will…

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Main Street Mixer

March 31 @ 5:30 pm - 6:30 pm

Join local entrepreneurs and Gloucester Main Street members, as we kick off our first ever 'Main Street Mixer' This virtual event will highlight local businesses, engage guests in custom cocktail construction (and sipping), and allow entrepreneurs from the Hampton Roads and Middle Peninsula area to learn more about one another's businesses...all from the comfort and safety of our homes or offices. Our event will be held virtually (link to be sent out after registration) and will be free to Main…

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April 2021


April 3 @ 9:00 am - 11:00 am
Yolanda’s, 6658 Main Street
Gloucester, VA 23061 United States

Are you on the HUNT for something EGG-citing to do Easter weekend??? Whether you are young in age OR at heart, the Gloucester Village EGGSTRAVAGANZA on Main Street Scavenger Hunt is FUN for ALL!!! Just bring a pen and wear comfy shoes as you roam our Downtown, following the clues! EACH ticket purchased includes: an entry to win a $50 Patriots Grill gift certificate, a clue filled Scavenger Hunt Form, and a fun-filled goodie bag to include a craft, toys, candy and sweet treats from…

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September 2021


Last Call Before Fall

September 5 @ 12:00 pm - 5:00 pm
Split Enz Salon, 6596 Main Street
Gloucester, VA 23061 United States

Who's ready for an event??!!!!!!  We sure are!!! Gloucester Main Street Association is pleased to announce a NEW FUN event, LAST CALL BEFORE FALL! Join us on Sunday, September 5 from Noon-5PM on the lawn of Split Enz Salon (Tabb House)- 6596 Main Street, Gloucester. LIVE music performed by the JACKASS FLATS ! Everyone is invited to come out and enjoy domestic and craft brews, hard cider, and non-alcoholic options. Food Trucks and vendors will also be on-hand. Tickets are…

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October 2021

Sidewalk Sale on Main

October 16 @ 10:00 am - 5:00 pm
Gloucester Main Street, Main Street
Gloucester, VA 23061 United States

Looking for some end of season savings? Well head to your Downtown Gloucester Village for special savings from multiple great local small businesses!

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