Chocolate Escape

Sample chocolate desserts at participating downtown restaurants, enjoy special discounts and treats at participating shops, listen to live music, and pamper yourself during the annual Chocolate Escape!

Diners and shoppers will have the chance to make Valentine’s Day reservations and purchase gifts for loved ones or just browse. Old Town Winchester offers fine dining, artisan shops and specialty boutiques, florists, jewelry stores as well as a day spa and a salon. Escape to Old Town Winchester for Valentine shopping specials and indulgent chocolate morsels.

Stay tuned for more details and a list of participating businesses.

Holiday Open House at Willow Moon Farm

We are so excited to announce our ANNUAL OPEN HOUSE here on the farm on December 18th from 10am – 3pm!
What can you expect?

Our apothecary building open- where we will have all of our products and items that we offer displayed for you to shop, ask questions and talk with Sara (owner) about the farm. You can expect to see our unique skincare products, soy candles, goats milk soaps, herbal remedies, Certified Naturally Grown eggs, canned goods, dried herbs and much more. All items are made/produced here on the farm from scratch!

Whisked Sugar Bakeshoppe will be set up with a variety of baked goods- cakes, cupcakes, cookies & hot cocoa bombs! All handmade and locally made here in Gore.
1 free raffle ticket to each family that will have a chance to win a gift basket full of our products and an item from our featured baker.
Farm tours where you can visit our livestock and get all of the goat snuggles.
Hot cocoa bar
Christmas music
We hope you will visit us to see our farm and see how much we have expanded this past year!
We look forward to seeing you and spreading holiday cheer!

Windependent Weekend

Join us for Windependent Weekend: a celebration of the local businesses indie community that makes Winchester special.

Holiday shopping is just around the corner—and so are the best places to do it! Keep your purchases local and discover all the good that supporting small businesses can do.

Enjoy special sales, discounts, and promotions at Old Town businesses during this two day event.

Holiday Pop Up Shop

Easely Created is hosting a socially-distanced Holiday POP Up Shop.

You can shop in person on small business Saturday (November 28th) at Easely Created in downtown Winchester from 11-8pm or virtually from November 28th – December 6th. All artist/vendors are local and each creation is handmade with love!

Check out the holiday shopping group
and get updates on highlighted vendors, when shopping opens and when crafters post new items!

Join us as we continue the effort to support small businesses and local makers.

Mom2Mom Consignment Sale


Are you looking for great deals on children’s items at a fraction of the retail price? Then shopping at the Mom 2 Mom Consignment Sale is for you!

*Prices are AWESOME! Save 30-90% OFF retail!
*Items inspected for quality
*Organized for your shopping pleasure
*Shop from HUNDREDS of families at ONCE!
*Cash and major credit/debit accepted

Public Shopping Hours:

Fri, March 27: 9am-8pm ($5 admission per adult)
Sat, March 28: 9am-7pm
Sun, March 29: 9am-2pm (Many items 50% off)

Consignor registration and details at

Holly Jolly Old Town Celebration

Come spend some time in Old Town this holiday season during our Holly Jolly Celebration on December 14th!

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.

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.

More information and schedule of events


Old Town Christmas Party

Join the Polka Dot Pot, Once Upon a Find, and Fellowship of the Sip for Christmas activities on several weekends in December.

• Open Houses with Gift baskets and discount coupons!
• Christmas markets on the South Loudoun Mall!
• Live music concert at the Fellowship of the Sip!
• Stories about Christmas celebrations around the world and treats to taste!
• Free seminar!

Christmas Party Calendar:
7th, 8th & 9th — Open houses, outdoor markets with Christmas gifts, lights, lamps, tree ornaments, pottery, candles,teas and more at all three locations. Saturday 8th — 9am-11am, free seminar – Color Your Stress Away – Art and Music Therapy session at the Fellowship of the Sip

14th, 15th & 16th — Open houses, Christmas Markets on the South Loudoun Street Mall- more gifts & services offered, Christmas teas and cookies to taste! Visit all three locations! Saturday 15th — 2pm-3pm – Melanie Miller – Free Christmas concert – songs and melodies on electric piano and ukulele at the Fellowship of the Sip (weather permitting – outdoor)

20th, 21st, 22nd & 23rd — Last minute Christmas shopping and holiday treats and drinks tasting! Gift certificates & cards available. Saturday 22nd – 2pm-3pm – Chef Christopher McAvoy tells stories about Christmas celebrations all around the world – samples of treats to taste at the Fellowship of the Sip.

Christmas Open House

Please join us for our Christmas Open House! Friday, Dec 14th from 12-5 pm. Stop by and have some holiday cheer with us and sample our delicious treats! Bring a non-perishable food item for our food drive for a very, very needy family that we are helping this year. All donations are appreciated.

Holiday Bazaar

Millbrook High School band boosters holiday bazaar will be Saturday December 1st, 2018 from 8am-2pm. It will be held in the cafeteria of Millbrook High School. The holiday bazaar will include 56 local vendors, local foods, pictures with Santa (parents may take their own free pictures or there will be a professional photographer on site) and raffles all day!

Admission is free.