Holly Jolly Celebration

Enjoy the holidays in Old Town at the Annual Holly Jolly Celebration on December 14th, 10 a.m. – 5 p.m.!

Enjoy caroling and holiday activities including free holiday wagon rides from 1-4 p.m. Specials at shops and restaurants all day.

Returning for a second year, shop at the Old Town Farmers Market – Holiday Market from 11 a.m.-5 p.m. Here you will find local in-season farm goods including varieties of garlic, squash, heritage breed pork, jams and jellies, fresh small batch roasted coffee beans, spice rubs and seasonings, artisan chocolates and cake pops, natural health and beauty products, festive iced cookies and gingerbread kits, botanical ornaments and home decor items, homemade novelty soaps, and handcrafted jewelry and hair accessories.  Sip on hot cocoa and enjoy warm frosted nuts and fresh kettle corn while you shop!

Children can create a holiday craft while waiting to meet Santa Claus at Santa’s Headquarters from 10 a.m. – 2 p.m. at the Godfrey Miller House (28 S. Loudoun Street).

Enjoy holiday carols throughout Old Town Winchester provided by local choral groups as well as a free petting zoo featuring alpacas, historic walking tours, craft and gift wrapping stations, entertainment by Jimi the Juggling Elf, and more!

Free horse drawn wagon rides will be offered from 1-4 p.m. Meet in front of the Old Courthouse (20 N. Loudoun Street) to pick up a timed ticket beginning at 1pm. Tickets go fast! No need to stand in line! Enjoy holiday shopping and dining in Old Town and return to the wagon area prior to your ticket time.

Families can visit Handley Library from 1-3 p.m. for classic holiday movies as well as interactive stations and make-and-take crafts.

Thank you to City of Winchester Parks & Recreation for assisting with Santa’s Headquarters!

Click to download the 2019 Holly Jolly Full Schedule

Holly Jolly Schedule:

10am-5pm – Caroling throughout the day.

10am-2pm – Santa’s Headquarters at the Godfrey Miller Center. (28 S. Loudoun Street)

11am-5pm – Holiday Market. Vendors include:

  • Andrea’s Goodies (Winchester, VA) – Cut out sugar cookies, oatmeal cinnamon chip & sea salt bars, handmade marshmallows, chocolate chip cookies, gingerbread house kits, cookie kits.
  • Boward Family Farm (Augusta, WV) – Garlic by the pound and braids, garlic pepper finishing salts, dried peppers, jams and jellies, hot sauce, pickled veg. All natural handcrafted small batch body care products such as body butters, lip balms, sugar body scrubs, natural deodorant, tooth powder, skin salves, essential oil sprays and roll-ons. Handmade Adirondack pack baskets from Ironwood Farms Basketry.
  • Creative Concessions (Cross Junction, VA) – Fresh kettle corn, frosted nuts, cotton candy, hot cocoa.
  • Hello Haberdashery (Capon Bridge, WV) – Hair accessories, top hats, earrings, pins, fascinators, circlets, cuff links, floral crowns.
  • Old Valley Pike Soap Company (Strasburg, VA) – Cold process soaps, novelty shape soaps, body butters.
  • R&E Chocolates (Strasburg, VA) – Artisanal truffles, chocolate covered cookies, chocolate lollipops, cake pops.
  • Scruples Coffee (Front Royal, VA) – Fresh roasted coffee beans, sugar scrubs, BBQ rubs.
  • Smoky Bend Farm (Berkeley Springs, WV) – In-season produce, Mangalista pork, heritage breed pork.
  • Valley Stream Marketplace (Winchester, VA) – Botanical crafts including dried wreaths, floral Christmas ornaments, potpourri, sachets, paperwhite narcissus, felted items including soaps and ornamental crafts.

11am-3pm – Petting Zoo featuring alpacas from Poverty Ridge Farm (Old Courthouse Lawn)

11am-3pm – Snow Making and Gift Wrapping with Shenandoah Valley Discovery Museum (21 S. Loudoun Street)

12pm-2pm – Holiday Historic Walking Tours with Preservation of Historic Winchester. Meet in front of the Old Courthouse (20 N. Loudoun Street)

1pm-4pm – FREE Horse Drawn Wagon Rides. Meet in front of the Old Courthouse (20 N. Loudoun Street) to pick up a time ticket beginning at 1 p.m. Tickets go fast! No need to stand in line! Enjoy holiday shopping and dining in Old Town and return to the wagon area prior to your ticket time.

1pm-3pm – Classic Holiday Movies at Handley Library. Families can enjoy movies, popcorn, interactive stations, and a make-and-take craft. (100 W. Piccadilly Street)

  • 1pm: Frosty the Snowman
  • 2pm: Rudolph the Red Nose Reindeer
  • 3pm: A Charlie Brown Christmas

2pm-3pm – Storytime with the Grinch at The Hideaway Café. Visit with the Grinch and enjoy classic holiday stories. (141 S. Loudoun Street)

2pm-5pm – Strolling with Santa. Greet Santa along the Loudoun Street Mall as he spreads holiday cheer!


Old Town Specials and Promotions:

The Black Rose, 11 S. Loudoun St.
25-75% savings on items in the GIFT GALLERY. Small coffee and sweet treat; $4.00 in OUR LOUNGE. Book a facial on December 14th and save 25% in THE SKINCARE STUDIO. Gift Cards available for holiday giving. Outdoor display, weather permitting.

Blue Peacock Antiques, 116 N. Loudoun St.
Holly Jolly Jingle Bell Event Sale. Enjoy shopping sales and cookies, Hot Apple Cider or Hot Chocolate and Nostalgic Christmas music for customers to enjoy while browsing through our bountiful Antiques and Vintage items.  Outdoor display, weather permitting.

Bright Box Theater, 115 N. Loudoun St.
10% discount on gift certificates.

Fellowship of the Sip Restaurant and Tea House, 33 S. Loudoun St.
Free samples and special treats for purchase. Post-Holly Jolly free promotional event for the Good Food Lovers and Promoters Club with Christmas focus 5:30-7pm.

Flavor Pourfection Artisian Olive Oil and Vinegar Tap Room, 17 S. Loudoun St.
Holly Jolly Special. Spend $30 or more and receive a free sample size bottle of oil or vinegar. Excludes specialty products. Outdoor display with free samples, weather permitting.

Handworks Gallery, 150 N. Loudoun St.
Receive a $5 gift certificate for every $50 spent during Holly Jolly. No limit!

Knit 1 Purl 2, 20 W. Boscawen St.
20% off all yarn.

Knitters Magic, 212 S. Loudoun St.
Small gift with purchase.

Love’s Affect Jewelry, 3 S. Loudoun St.
30% store wide.

LoX Salon, 209 E. Boscawen St.
2 complimentary extensions (red & green) with any blonding service for the holidays. 10% off pre-made gift sets with complimentary makeup bag.

Mountain Trails, 115 N. Loudoun St.
Holly Jolly Sales! All footwear 20-50% off, backpacks 20-40% off, travel luggage 30% off, rain jackets up to 40% off (excluding Patagonia), camp furniture 20% off, sleeping bags 30% off.

Murphy Beverage Company, 167 N. Loudoun St.
Homemade Christmas cookie & wine pairing, 2-5pm, with Virginia Imports. Gluewein also available. Special appearance by Krampus. 

Once Upon A Find, 48 S. Loudoun St.
One Free plaid ornament ($10.00 value) with a $25.00 purchase, also $5.00 Christmas discount coupon on a $25.00 purchase. Many store wide discounts, complimentary cookies and candy canes.

Posh Pets Boutique, 156 N. Loudoun St.
Sales of 30% off all Christmas themed pet toys, 20% off all iced dog cookies, 20% off all Christmas themed pet clothing and accessories, and 25% off all beds and crate mats.

The Quirky Closet, 15 E. Boscawen St.
25% off the entire store.

Scarpa Alta, 10 S. Loudoun St.
20% off all boots sale.

Scout Troop 2, 22 S. Loudoun St.
Christmas trees and holiday knick-knacks.

Tin Top Art + Handmade, 130 N. Loudoun St.
Holly Jolly Card Sale! 25% off all holiday cards (singles and packs).

Valley Flag Company, 20 W. Boscawen St.
20% off all novelty flags.

Wilkins’ ShoeCenter, 7 S. Loudoun St.
Bring your Christmas spirit and shop with us for a 15% discount (exclusions apply). Join us in donning your favorite ugly Christmas sweater and shop, snack and be MERRY!

Worlds Away Escape, 9 N. Loudoun St.
Take 15% off gift certificates purchased in store or online with code hollyjolly.

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