Wine Events and Things to do in Gloucester Courthouse, VA

First Friday Karaoke at City Vino
Fri, Jul 3, 7:00 PM + 6 more
Fredericksburg · 100 Hanover St
First Friday Karaoke at City Vino
Fri, Jul 3, 7:00 PM + 6 more
Fredericksburg · 100 Hanover St
A Murder Mystery Adventure at The Estate at River Run
Fri, Jun 19, 6:45 PM
Maidens · The Estate At River Run
A Murder Mystery Adventure at The Estate at River Run
Fri, Jun 19, 6:45 PM
Maidens · The Estate At River Run
Together for Tanzania Gala: Big Band Evening of Impact
Fri, Jul 24, 6:00 PM
Powhatan · Fairview Farm Events
Together for Tanzania Gala: Big Band Evening of Impact
Fri, Jul 24, 6:00 PM
Powhatan · Fairview Farm Events
Sales end soon
City Vino's Got Smooth Jazz with Gregory Amos
Saturday at 7:00 AM
Fredericksburg · City Vino
Sales end soon
City Vino's Got Smooth Jazz with Gregory Amos
Saturday at 7:00 AM
Fredericksburg · City Vino
Gatsby on the James | A Summer Signature Event at The Estate at River Run
Fri, Jun 26, 7:30 PM
Maidens · The Estate At River Run
Gatsby on the James | A Summer Signature Event at The Estate at River Run
Fri, Jun 26, 7:30 PM
Maidens · The Estate At River Run
The Port Oysteria & Brewery feat. Uptown Smokes
Thursday at 6:00 PM
Fredericksburg · 106 George St
The Port Oysteria & Brewery feat. Uptown Smokes
Thursday at 6:00 PM
Fredericksburg · 106 George St
Sip and Spa Sanctuary
Sat, Jul 25, 10:00 AM
Fredericksburg · Vibin' With Val (Valerie Rosemond Settles, Vintner)
Sip and Spa Sanctuary
Sat, Jul 25, 10:00 AM
Fredericksburg · Vibin' With Val (Valerie Rosemond Settles, Vintner)
2026 CrabDaddy Bus Trip Oct. 10th $99 Departing Hampton Roads
Sat, Oct 10, 6:30 AM
Jarvisburg · Sanctuary Vineyards Outer Banks Winery
2026 CrabDaddy Bus Trip Oct. 10th $99 Departing Hampton Roads
Sat, Oct 10, 6:30 AM
Jarvisburg · Sanctuary Vineyards Outer Banks Winery
2026 CrabDaddy Bus Trip $99pp -on Oct. 10th, Departing Hampton Roads
Sat, Oct 10, 6:30 AM
Jarvisburg · Sanctuary Vineyards Outer Banks Winery
2026 CrabDaddy Bus Trip $99pp -on Oct. 10th, Departing Hampton Roads
Sat, Oct 10, 6:30 AM
Jarvisburg · Sanctuary Vineyards Outer Banks Winery
Sundresses and Cigars
Thursday at 5:00 PM + 7 more
Portsmouth · Admiral’s Steak & Seafood
Sundresses and Cigars
Thursday at 5:00 PM + 7 more
Portsmouth · Admiral’s Steak & Seafood
City Vino Hosts the Confident Rooster Society Improv
Fri, Jun 26, 7:00 PM + 1 more
Fredericksburg · City Vino
City Vino Hosts the Confident Rooster Society Improv
Fri, Jun 26, 7:00 PM + 1 more
Fredericksburg · City Vino
The Wine Cirlce Meetup- Sundresses & Sips Edition
Sun, Jul 12, 1:00 PM
Upper Marlboro · Two Lions Vineyards
The Wine Cirlce Meetup- Sundresses & Sips Edition
Sun, Jul 12, 1:00 PM
Upper Marlboro · Two Lions Vineyards
Ride for Mutts and Pig Pickin'
Sat, Jul 11, 12:00 PM
Spotsylvania Courthouse · 1781 Brewing Company
Ride for Mutts and Pig Pickin'
Sat, Jul 11, 12:00 PM
Spotsylvania Courthouse · 1781 Brewing Company
Mask & Mimosas
Sat, Jul 11, 12:00 PM
Cambridge · The Phillips Packing House company
Mask & Mimosas
Sat, Jul 11, 12:00 PM
Cambridge · The Phillips Packing House company
Sea Glass and Coastal Arts Show
Tue, Jun 16, 10:00 AM + 1 more
Corolla · 1100 Club Rd
Sea Glass and Coastal Arts Show
Tue, Jun 16, 10:00 AM + 1 more
Corolla · 1100 Club Rd
The LAFF'N JAZZ Lounge
Fri, Jun 19, 7:00 PM + 5 more
Salisbury · Inspire Gallery
The LAFF'N JAZZ Lounge
Fri, Jun 19, 7:00 PM + 5 more
Salisbury · Inspire Gallery
Going fast
Tobias Cortez Live: Summer All White Party
Saturday at 2:00 PM
Louisa · 206 Harris Creek Rd
Going fast
Tobias Cortez Live: Summer All White Party
Saturday at 2:00 PM
Louisa · 206 Harris Creek Rd
Come join us for a colorful afternoon painting !
Sun, Jun 14, 2:00 PM
Blackstone · 120 W Broad St
Come join us for a colorful afternoon painting !
Sun, Jun 14, 2:00 PM
Blackstone · 120 W Broad St
Going fast
Brandywine Social w/ Open Mic Karaoke @ Piano Keys Lounge June 9th
Tomorrow at 6:00 PM + 5 more
Brandywine · Piano Keys Restaurant and Lounge
Going fast
Brandywine Social w/ Open Mic Karaoke @ Piano Keys Lounge June 9th
Tomorrow at 6:00 PM + 5 more
Brandywine · Piano Keys Restaurant and Lounge

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Trends in Gloucester Courthouse

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First Friday Karaoke at City Vino

First Friday Karaoke at City Vino

A Murder Mystery Adventure at The Estate at River Run

A Murder Mystery Adventure at The Estate at River Run

Together for Tanzania Gala: Big Band Evening of Impact

Together for Tanzania Gala: Big Band Evening of Impact

City Vino's Got Smooth Jazz with Gregory Amos

City Vino's Got Smooth Jazz with Gregory Amos

Gatsby on the James | A Summer Signature Event at The Estate at River Run

Gatsby on the James | A Summer Signature Event at The Estate at River Run

The Port Oysteria & Brewery feat. Uptown Smokes

The Port Oysteria & Brewery feat. Uptown Smokes

Sip and Spa Sanctuary

Sip and Spa Sanctuary

2026 CrabDaddy Bus Trip Oct. 10th $99 Departing Hampton Roads

2026 CrabDaddy Bus Trip Oct. 10th $99 Departing Hampton Roads

2026 CrabDaddy Bus Trip $99pp -on Oct. 10th, Departing Hampton Roads

2026 CrabDaddy Bus Trip $99pp -on Oct. 10th, Departing Hampton Roads

Sundresses and Cigars

Sundresses and Cigars

City Vino Hosts the Confident Rooster Society Improv

City Vino Hosts the Confident Rooster Society Improv

The Wine Cirlce Meetup- Sundresses & Sips Edition

The Wine Cirlce Meetup- Sundresses & Sips Edition

Ride for Mutts and Pig Pickin'

Ride for Mutts and Pig Pickin'

Mask & Mimosas

Mask & Mimosas

Sea Glass and Coastal Arts Show

Sea Glass and Coastal Arts Show

The LAFF'N JAZZ Lounge

The LAFF'N JAZZ Lounge

Tobias Cortez Live: Summer All White Party

Tobias Cortez Live: Summer All White Party

Come join us for a colorful afternoon painting !

Come join us for a colorful afternoon painting !

Brandywine Social w/ Open Mic Karaoke @ Piano Keys Lounge June 9th

Brandywine Social w/ Open Mic Karaoke @ Piano Keys Lounge June 9th

Popular events

Things to do around Gloucester Courthouse

Trends in Gloucester Courthouse

1. Gloucester moose lodge calendar

2. Kid friendly events

3. Car shows

4. Gloucester wine festival

5. Speed dating

6. Live music

7. Wine

8. Nu vibez lounge

9. Motherday brunch

10. Kids events

11. Youth football camp

12. Woodmenlifevaseniors26