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Top Foodie Things to Do During the Holidays in Winchester, VA

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Bring Your Own GingerBread House


📅 Wed, Dec 4th from 4:00 pm to 8:00 pm

Winchester Brew Works

BYOGBH (Bring Your Own GingerBread House) and help us create a Winter Village in the brewery! You provide the Gingerbread house, and we’ll provide the Christmas tunes and hot cocoa!

Tinsel Tavern


📅 Wed, Dec 4th from 5:00 pm to 10:00 pm

18th Rebellion

Festive cocktails, cozy vibes, and ALL the holiday feels. Instagram worthy decor, signature drinks, and a vibe that's pure holiday magic. No cover. Group reservations available for 8+ only. Open Friday - Saturday 5 pm to midnight and Wednesday - Thursday 5 pm to 10 pm

Tinsel Tavern


📅 Thu, Dec 5th from 5:00 pm to 10:00 pm

18th Rebellion

Festive cocktails, cozy vibes, and ALL the holiday feels. Instagram worthy decor, signature drinks, and a vibe that's pure holiday magic. No cover. Group reservations available for 8+ only. Open Friday - Saturday 5 pm to midnight and Wednesday - Thursday 5 pm to 10 pm

Santa Crawl After Party


📅 Fri, Dec 6th

The Monument

Jack Fire Lodge


📅 Fri, Dec 6th

The Monument

The patio will be open for weekends through December. Includes hot drinks (boozy optional), fire pits, smores, treats and snowblowers.

3rd Annual Santa Bar Crawl


📅 Fri, Dec 6th from 4:00 pm to 9:00 pm

Old Town Winchester

Santa Bar Crawl Locations 2024: 50/50 Tap House, Benny’s Pizza, Broken Window Brewing, Macado’s, Paladin Downtown, Piccadilly’s Public House, Roma Old Town - Fired Pizzeria, Sexi-Mexi Burritos, The Monument, The Wine Room at Taylor Pavilion, Union Jack Pub & Restaurant, Vibrissa Beer, Village Square Restaurant, Water Street Kitchen, Willie Sutton’s, Winchester Brew Works, Winchester Cider Works

Winchester Old Town Winter Village


📅 Fri, Dec 6th from 4:00 pm to 8:00 pm

Old Town Winchester

Tinsel Tavern


📅 Fri, Dec 6th from 5:00 pm to 12:00 am

18th Rebellion

Festive cocktails, cozy vibes, and ALL the holiday feels. Instagram worthy decor, signature drinks, and a vibe that's pure holiday magic. No cover. Group reservations available for 8+ only. Open Friday - Saturday 5 pm to midnight and Wednesday - Thursday 5 pm to 10 pm

Jack Fire Lodge


📅 Sat, Dec 7th

The Monument

The patio will be open for weekends through December. Includes hot drinks (boozy optional), fire pits, smores, treats and snowblowers.

Mulled Wine Holiday Headquarters


📅 Sat, Dec 7th from 9:00 am to 5:00 pm

The Hideaway Cafe

We know you love mulled wine (Gluhwein). Visit The Hideaway Cafe for roasted chestnuts, horse-drawn carriage rides, visits with Santa, blacksmithing and wood turning demonstrations, crafts and vending, and a ton more.

Winchester Old Town Winter Village


📅 Sat, Dec 7th from 11:00 am to 8:00 pm

Old Town Winchester

Tinsel Tavern


📅 Sat, Dec 7th from 5:00 pm to 12:00 am

18th Rebellion

Festive cocktails, cozy vibes, and ALL the holiday feels. Instagram worthy decor, signature drinks, and a vibe that's pure holiday magic. No cover. Group reservations available for 8+ only. Open Friday - Saturday 5 pm to midnight and Wednesday - Thursday 5 pm to 10 pm

Mulled Wine Holiday Headquarters


📅 Sun, Dec 8th from 9:00 am to 4:00 pm

The Hideaway Cafe

We know you love mulled wine (Gluhwein). Visit The Hideaway Cafe for roasted chestnuts, horse-drawn carriage rides, visits with Santa, blacksmithing and wood turning demonstrations, crafts and vending, and a ton more.

Winchester Old Town Winter Village


📅 Sun, Dec 8th from 11:00 am to 4:00 pm

Old Town Winchester

Ugly Seater Brunch


📅 Sun, Dec 8th from 11:30 am to 2:30 pm

Village Square Restaurant

3-Course Brunch for $34.99 paired with $0.01 Mimosas & Bloody Marys

Tinsel Tavern


📅 Wed, Dec 11th from 5:00 pm to 10:00 pm

18th Rebellion

Festive cocktails, cozy vibes, and ALL the holiday feels. Instagram worthy decor, signature drinks, and a vibe that's pure holiday magic. No cover. Group reservations available for 8+ only. Open Friday - Saturday 5 pm to midnight and Wednesday - Thursday 5 pm to 10 pm

Rabbit Hole Bourbon Tasting


📅 Wed, Dec 11th from 6:00 pm to 8:00 pm

Willie Sutton's Saloon

A portion of the proceeds will go to Watts Winchester Area Temporary Shelter (WATTS). $75 per person. Ticket includes charcuterie and cocktail hour, soup, entree, dessert, and bourbon tasting led by a Rabbit Hole Representative.

Tinsel Tavern


📅 Thu, Dec 12th from 5:00 pm to 10:00 pm

18th Rebellion

Festive cocktails, cozy vibes, and ALL the holiday feels. Instagram worthy decor, signature drinks, and a vibe that's pure holiday magic. No cover. Group reservations available for 8+ only. Open Friday - Saturday 5 pm to midnight and Wednesday - Thursday 5 pm to 10 pm

Live Music w/ Jimmy Lee


📅 Fri, Dec 13th

Paladin Downtown

Jack Fire Lodge


📅 Fri, Dec 13th

The Monument

The patio will be open for weekends through December. Includes hot drinks (boozy optional), fire pits, smores, treats and snowblowers.

Tinsel Tavern


📅 Fri, Dec 13th from 5:00 pm to 12:00 am

18th Rebellion

Festive cocktails, cozy vibes, and ALL the holiday feels. Instagram worthy decor, signature drinks, and a vibe that's pure holiday magic. No cover. Group reservations available for 8+ only. Open Friday - Saturday 5 pm to midnight and Wednesday - Thursday 5 pm to 10 pm

Free Tasting Event


📅 Fri, Dec 13th from 5:00 pm to 7:00 pm

The Beer & Wine Shop

Cushwa Brewing Co and Free Run Wine Merchants. Follow us The Beer & Wine Shop on Facebook or Instagram for the tasting lineup.

Noonday Pop Up


📅 Sat, Dec 14th

Espresso Bar & Cafe

Acoustic singer/songwriter, Colin Bouchillo

Jack Fire Lodge


📅 Sat, Dec 14th

The Monument

The patio will be open for weekends through December. Includes hot drinks (boozy optional), fire pits, smores, treats and snowblowers.

Poetry Reading with Randina Sheldon


📅 Sun, Dec 15th

Espresso Bar & Cafe

Lunch With Santa


📅 Sun, Dec 15th from 11:30 pm to 2:30 pm

Cafe Del Sol

Harry Potter Trivia


📅 Wed, Dec 18th

Dividing Creek Beer Company

Tinsel Tavern


📅 Wed, Dec 18th from 5:00 pm to 10:00 pm

18th Rebellion

Festive cocktails, cozy vibes, and ALL the holiday feels. Instagram worthy decor, signature drinks, and a vibe that's pure holiday magic. No cover. Group reservations available for 8+ only. Open Friday - Saturday 5 pm to midnight and Wednesday - Thursday 5 pm to 10 pm

Holliday PJ Party


📅 Thu, Dec 19th from 4:00 pm to 8:00 pm

Winchester Brew Works

Dress in your favorite, cozy PJs and sip on some free hot cocoa and eat some Christmas cookies!

Country Music Night


📅 Fri, Dec 20th

Milano's Ristorante & Bar

Jack Fire Lodge


📅 Fri, Dec 20th

The Monument

The patio will be open for weekends through December. Includes hot drinks (boozy optional), fire pits, smores, treats and snowblowers.

Drag Bingo


📅 Fri, Dec 20th from 10:00 pm to 11:00 pm

50/50 Taphouse

Christmas Dance Party


📅 Sat, Dec 21st

Milano's Ristorante & Bar

Ugly Sweater Party


📅 Sat, Dec 21st

The Monument

Jack Fire Lodge


📅 Sat, Dec 21st

The Monument

The patio will be open for weekends through December. Includes hot drinks (boozy optional), fire pits, smores, treats and snowblowers.

Brunch w/ Santa


📅 Sun, Dec 22nd from 10:00 am to 2:00 pm

Willie Sutton's Saloon

DJ Brunch


📅 Sun, Dec 22nd from 11:30 am to 2:30 pm

Village Square Restaurant

Come Dressed as someone in Santa’s Village (Santa, Mrs. Clause, an Elf or Reindeer!). 3-Course Brunch for $34.99 paired with $0.01 Mimosas & Bloody Marys

Christmas Eve Dinner


📅 Tue, Dec 24th from 12:00 pm to 8:00 pm

Village Square Restaurant

A merry evening of great food, cozy atmosphere and even better company!

Live Music w/ Jimmy Lee


📅 Fri, Dec 27th

Paladin Downtown

Jack Fire Lodge


📅 Fri, Dec 27th

The Monument

The patio will be open for weekends through December. Includes hot drinks (boozy optional), fire pits, smores, treats and snowblowers.

Jack Fire Lodge


📅 Sat, Dec 28th

The Monument

The patio will be open for weekends through December. Includes hot drinks (boozy optional), fire pits, smores, treats and snowblowers.

DJ Brunch


📅 Sun, Dec 29th from 11:30 am to 2:30 pm

Village Square Restaurant

Bubbly and Bright Brunch to End the Year. (Glitter and Sparkle attire). 3-Course Brunch for $34.99 paired with $0.01 Mimosas & Bloody Marys

10-Course New Year's Eve Menu


📅 Tue, Dec 31st

Savour

New Years Eve


📅 Tue, Dec 31st from 11:30 am to 12:00 pm

Village Square Restaurant

On New Years open for lunch from 11:30 am - 2:30 pm. Will reopen at 4 pm for dinner. We will close at 11 pm.

New Years Eve 2024 - Gods & Goddesses


📅 Tue, Dec 31st from 7:00 pm to 12:00 am

Winchester Brew Works

Whew boy this has been a YEAR. Let's try to shake off what we can and ring in the New Year together! Grab your toga and your Mjollni and dance the night away with us! Custom dinner menu by our bestie, Billy Sous. Tickets are $60 + tax (includes dinner from Billy Sous, desserts from Crumbs and Crumbles, champagne toast at midnight, dancing till your grape leaves fall off, and general merriment!).

New Year's Eve


📅 Tue, Dec 31st from 8:00 pm to 12:00 am

The Wine Room at Taylor Pavilion

Sunday Brunch


📅 Sun, Jan 5th from 10:00 am to 2:00 pm

Sexi-Mexi Burrito Bar

Starting in January, brunch every Sunday.

Maestro Dobel Tequila Dinner


📅 Thu, Jan 16th from 6:00 pm to 9:00 pm

Village Square Restaurant

Dive into the Tequila World with for a 4-Course Dinner paired with Maestro Dobel Tequilas! Reservations are required.