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Happy hours in Winchester, VA

In Winchester, the lowest price on the list is $1 Oysters on the Half Shell at Village Square Restaurant. Most happy hours in Winchester run 4–6pm, and mostly on weekdays. Explore 13 happy hours across 8 restaurants in Winchester, plus 43 specials at 21 restaurants. The top 5 menus are below, then 2 more from Shawneeland (4 miles) and Front Royal (13 miles).

  • 8restaurants
  • 13happy hours

Happy hours in and near Winchester

  1. Glory Days Grill

    130 Featherbed Ln
    Winchester, VA 22601

    Happy Hour

    • Daily · All day

    1 more happy hour on Mon–Fri

    See on the map

    Updated Oct 25, 2026

    Wine

    • House Wine (glass)$6.50

    Spirits

    • Tito’s Handmade Vodka$7.00
    • Tito’s Handmade Vodka (double)$12.00
    • Buffalo Trace$7.00
    • Buffalo Trace (double)$12.00
    • Jameson$9.00
    • Jameson (double)$15.00

    Cocktails

    • Homerun Margarita 24oz$7.50
    • White Sangria 24oz$7.00
    • Red Sangria 24oz$7.00

    Beer

    • Busch Light pint (16oz)$3.25
    • Busch Light 22oz$5.25
    • Bud Light pint (16oz)$4.75
    • Bud Light 22oz$6.75
  2. Union Jack Pub and Restaurant

    101 N Loudoun St
    Winchester, VA 22601

    Happy Hour

    • Mon, Tue · 4–7 pm
    • Wed · 4–8 pm
    • Thu, Fri · 4–7 pm
    See on the map

    Updated Oct 25, 2026

    Cocktails

    • House Margarita$5.00
    • House Moscow Mule$5.00
    • Cherry Almond$5.00

    Wine

    • Wine bottles50% off

    Spirits

    • House spirits$4.00
    • Rail shots$4.00

    Food

    • Spinach & Artichoke Dip
    • Loaded Fries
    • Soft Pretzels / Pretzels & Beer Cheese (3 count)

    Beer

    • Drafts$5.00
    • Domestic bottles/cans$3.00
    • Imported bottles/cans$4.00
  3. Village Square Restaurant

    103 N Loudoun St
    Winchester, VA 22601

    Happy Hour Menu

    Lounge and bar; patio if weather permitting

    • Mon–Fri · 4–6 pm

    4 more happy hours on Mon–Thu

    See on the map

    Updated Oct 25, 2026

    Food

    • Oysters on the Half Shell$1.00
    • Broiled Oyster$2.00
    • Old Bay Wings$1.50
    • Tide Water Twinkies$4.00
    • Crab & Pimento Cheese Dip$11.00

    and 2 more on the map

    Beer

    • All Draft Beer$4.00

    Cocktails

    • Watermelon Refresh$5.00
    • Aperol Spritz$5.00
    • Blueberry Matador$5.00
    • Old Fashioned$5.00
    • Peach Lemon Drop$5.00
    • French 75$5.00

    Wine

    • House Wine by the Glass$7.00
  4. Chili's Grill & Bar

    200 Featherbed Ln.
    Winchester, VA 22601

    Happy Hour

    • Mon–Fri · 3–6 pm
    See on the map

    Updated Oct 25, 2026

    Beer

    • Bud Light 16 oz$3.00
    • Miller Lite 16 oz$3.00
    • Coors Light 16 oz$3.00
    • Bud Light 22 oz$4.00
    • Modelo 16 oz$4.00

    and 5 more on the map

    Cocktails

    • Margarita of the Month$6.00
    • Tequila Classic Marg$7.00

    Wine

    • House Red & White Wine$5.00
  5. Oak Stone Craft Pizza and Bar

    1000 Valley Ave
    Winchester, VA 22601

    Happy Hour Wines

    • Mon–Fri · 3–6 pm
    See on the map

    Updated Oct 25, 2026

    Wine

    • Oak Stone House-Made Seasonal Sangria (glass)$5.00
    • La Remise de la Mordorée Dry Rosé, France (glass)$5.00
    • Sterling Pinot Grigio, CA (glass)$5.00
    • Sterling Merlot, CA (glass)$5.00
  6. Carrabba's Italian Grill

    Shawneeland, VA · 3.9 mi away

    231 Kernstown Commons Blvd
    Winchester, VA 22602

    Happy Hour

    Bar area

    • Daily · 4–7 pm
    See on the map

    Updated Oct 9, 2026

    Food

    • Spinach Arancini$5.00
    • Zucchini Fritte$5.00
    • Lasagne Dip$7.00
    • Mezzaluna Fritte$7.00
    • Shrimp Focaccia Bites$7.00

    and 3 more on the map

    Beer

    • Michelob ULTRA$3.00
    • Peroni$3.00

    Wine

    • Bonizio Rosso$5.00
    • Bonizio Bianco$5.00
    • Chloe Pinot Grigio$7.00
    • Mark West Pinot Noir$7.00
    • Coppola Diamond Cabernet Sauvignon$9.00
    • Kendall-Jackson Chardonnay$9.00

    Cocktails

    • Classic Red Sangria$5.00
    • Blood Orange Margarita$5.00
    • Rosé Sangria$7.00
    • Pomegranate Martini$7.00
    • Limoncello Spritz$7.00

    and 4 more on the map

    Spirits

    • Absolut$7.00
    • Bacardi$7.00
    • Lunazul Blanco$7.00
    • Jack Daniel's$7.00
    • Crown Royal$7.00

    and 2 more on the map

    Non-alcoholic

    • Amalfi Cooler$5.00
    • Prickly Pear Punch$5.00
  7. Houlihan's

    Front Royal, VA · 12.7 mi away

    101 Hospitality Drive
    Front Royal, VA 22630

    Happy Hour

    • Mon–Fri · 5–7 pm
    See on the map

    Updated Oct 9, 2026

    Cocktails

    • Well Cocktails (spirit + single mixer)$3.00
    • Traditional Margarita$5.00
    • Fresh Agave Margarita$5.00
    • Traditional Mojito$5.00
    • Long Island Ice Tea$5.00

    Food

    • Bottomless fries$6.00

    Beer

    • 12 oz Draft Beers50% off

We read each restaurant’s own website for its happy hours and specials, usually about once a month; this page was last updated October 25, 2026. Restaurants change their offers, so check with the restaurant before you go.

See all 8 happy hour menus in Winchester on the map

Friends toasting at an outdoor restaurant

Menus, times and prices

See every happy hour menu in Winchester.

Every happy hour in Winchester, with its menu, times and prices, on one map.

Happy hours in Winchester: questions

When is happy hour in Winchester?

Glory Days Grill runs it daily, all day. Union Jack Pub and Restaurant runs it Mon, Tue, 4–7 pm and Wed, 4–8 pm, and on other days. Village Square Restaurant runs it Mon–Fri, 4–6 pm. Choose Now on the map for the ones on right now.

What is the cheapest happy hour deal in Winchester?

The lowest price on the list is $1 Oysters on the Half Shell at Village Square Restaurant, then $3 Domestic bottles/cans at Union Jack Pub and Restaurant and $3 Bud Light 16 oz at Chili's Grill & Bar.

Where can I get happy hour food in Winchester?

Union Jack Pub and Restaurant and Village Square Restaurant have food on their happy hour menu.

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