Upcoming Events

2024 Christmas and Holiday Parade
Dec
7

2024 Christmas and Holiday Parade

The 2024 Christmas & Holiday Parade on Main Street is a festive celebration to kick off the holiday season. Join us for an enchanting afternoon filled with lights, music, and creative floats as they make their way down Main Street. Stick around after the parade for the annual tree lighting, sponsored by the Cook Foundation & Gloucester Main Street Association.

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Arts On Main: A “Celebration of the Arts" Soirée
Nov
16

Arts On Main: A “Celebration of the Arts" Soirée

Join Arts on Main at our annual Fall Fundraiser! At this popular event, guests will enjoy the musical stylings of award-winning musician Professor Amy Insley as well as drinks and heavy hors d'oeuvres by Gidi Gourmet! Soirée attendees will also be able to participate in a live/silent auction to win trips, experiences, and art that will be on display at Arts on Main for the month of November.

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Trick or Treat on Main Street
Oct
31

Trick or Treat on Main Street

Join us on Main Street for this year’s Halloween Trick or Treat on Thursday, October 31st! From 5 to 7 PM, enjoy a safe, fun-filled evening with plenty of costumes and candy. Main Street will be closed during the event to ensure a safe environment for everyone.

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The Fairfield Foundation's Historic House Party
Oct
12

The Fairfield Foundation's Historic House Party

The Fairfield Foundation hosts its 9th Annual Historic House Party at Exchange in Gloucester. Each year, Fairfield holds this exclusive event to celebrate the accomplishments of the year and raise funds for a new project. This June, the Richmond-based Cabell Foundation awarded Fairfield a $100,000 matching grant to restabilize the Rosewell Ruins. All money raised during the House Party will support this grant.

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Amazing Grace Flower Farm
Oct
8

Amazing Grace Flower Farm

Amazing Grace Flower Farm invites you to a delightful Sunday afternoon of fun, fellowship, and floral creativity! Learn how to design your own unique bouquet using locally grown flowers, guided by the farm’s owner, Varetta Hamlin. The workshop will take place at the York & Main Art Gallery on Sunday, October 27, from 2 - 4 PM.

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Oktoberfest
Oct
5

Oktoberfest

  • Heron Cove Way Gloucester, VA, 23061 United States (map)
  • Google Calendar ICS

Join Riverside's Sanders for their first annual Oktoberfest on October 5th, from 10 AM to 5 PM! Enjoy a day filled with fantastic food, unique vendors, and much more. Gloucester Brewing Company will be serving their finest local beers, and various local vendors will showcase their handmade creations. Best of all, entry is free!

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Sanders’ First Annual Oktoberfest
Oct
5
to Oct 8

Sanders’ First Annual Oktoberfest

The Gloucester Main Street Association is proud to sponsor Riverside's Sanders first annual Oktoberfest! Join Sanders this Saturday, October 5th, from 10 AM to 5 PM, for a day filled with fantastic food, unique vendors, and much more.

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Beaded Pumpkin Workshop with Dia Lawless
Sep
26

Beaded Pumpkin Workshop with Dia Lawless

Are you ready for fall? Make the first fall decoration of the season for your home! You will learn how to use metal, beads, wire, and ribbon to create a unique beaded pumpkin. This lovely beaded pumpkin is fun, festive, and easy to make! Leave with something you are proud to display and tell people you made. Come enjoy an evening that will bring in the season!

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Wine, Whiskey, and WhatNot Festival
Sep
21

Wine, Whiskey, and WhatNot Festival

Get ready to indulge your senses at this year’s Gloucester Wine, Whiskey, and WhatNot Festival on September 21st! This year, the Gloucester County Chamber of Commerce has turned up the excitement by adding whiskey tastings into the mix. Your ticket includes wine and whiskey tastings, plus incredible music by The Deloreans 80's Band.

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Split Enz September Social: "Love the Skin You're In"
Sep
19

Split Enz September Social: "Love the Skin You're In"

Split Enz Salon is hosting a September Social, “Love the Skin You’re In,” on September 19th, from 5 to 7 PM. Join the Split Enz Salon team as they celebrate the launch of Master Esthetician Hannah’s new suite of advanced skincare services, including dermaplaning, microcurrent, chemical peels, and more! The social will feature live demonstrations, opportunities to ask questions, product recommendations, makeup tutorials, and complimentary light refreshments and hors d’oeuvres. 

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Corey Arceneaux and the Zydeco Hot Peppers
Sep
14

Corey Arceneaux and the Zydeco Hot Peppers

Flat Iron Crossroads is bringing together three Virginia based bluegrass band on Saturday, 9/14/2024 to feature Rappahannock Crossing, Bill Jenkins & The Virginia Mountain Boys, and The Tidewinders headlining!

Doors open at 3:30pm and showtimes are 4:30pm, 6:00pm, and 7:30pm respectively. The food truck will be Island Time Delights, serving classic Filipino dishes! If the show is outdoors, bring a lawn chair! Children ages 12 & under are free.

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Impasto Palette Knife Workshop
Sep
14

Impasto Palette Knife Workshop

Join Rebecca West on Saturday, September 14 from 12:00 PM - 4:00 PM for an impasto palette knife workshop at Arts on Main!

Learn how to paint an impasto painting on a large-scale canvas! Impasto painting is an expressive and spontaneous form of painting where paint is applied on an area of a surface thick enough that the strokes are visible. In this class, you will learn how to use brushes and palette knives to create a textured floral painting. Rebecca will guide you from start to finish, there is no experience needed!

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Pressing Strings - Live at Flat Iron Crossroads
Aug
24

Pressing Strings - Live at Flat Iron Crossroads

Annapolis Maryland-based trio, Pressing Strings, loosely tied to indie, soul, and groove music is build by the instinct, imagination and inspiration of Jordan Sokel (Guitar/Vocals), Nick Welker (Bass, Vocals), and Justin Kruger (Drums, Vocals). They draw on iconic influences such as the usual suspects — Dylan, Marley, Simon, Withers, Al Green, Marvin Gaye, Led Zeppelin, etc., as well as some more under the radar artists like Taj Mahal, R.L. Burnside, Junior Kimbrough, and Nick Drake.

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Back To School Movie Night
Aug
17

Back To School Movie Night

Join the Gloucester Main Street Association for a delightful Back to School Movie Night featuring Disney/PIXAR's 'Up' at the Tabb House Lawn! Kick off the evening with pre-show games and activities starting at 6:30 PM, and settle in for the movie at dusk. Tickets are just $5 and include a small popcorn. Children 3 and under can attend for free.

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Jim Quick and Coastline - Live at Flat Iron Crossroads
Aug
17

Jim Quick and Coastline - Live at Flat Iron Crossroads

Over 25 years in the making, Jim Quick and Coastline, like their namesake the Atlantic Coastline Railroad, have been traveling the “tracks” of the southeast, and connecting with the hearts of loyal “Coastline Crazies.” Pulling from the threads of Soul, Blues, R&B, and Americana, Jim Quick and Coastline weave together their own genre of music known as Swamp Soul.

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Last Fair Deal with Dead Rise -  Live at Flat Iron Crossroads
Aug
10

Last Fair Deal with Dead Rise - Live at Flat Iron Crossroads

Last Fair Deal brings the experience of being at a Grateful Dead concert to life at this beautiful venue, Flat Iron Crossroads. The show will be opened by Dead Rise from 5:00-6:00pm. Last Fair Deal will perform from 6:30-9:30pm. We anticipate the show being outdoors with vendor, Rock Chakra and food truck, Get Cheesy. Doors open at 4:00pm – bring a lawn chair, blanket, and grab a drink at the FIX’ Bar inside.

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