ShenArtsFest

The Shenandoah Arts Council (ShenArts) presents a 2-day, juried, fine art festival, showcasing the work of artists from all over our region. Located along the Loudoun Street walking mall from Piccadilly St. to Cork St., visitors discover handmade-in-the-USA, original works of art across every medium, along with music, dance and a special flash mob event.

Careful vetting ensures the finest and most diverse offerings of sculpture, pottery, jewelry, photography, mixed-media, painting and more to suit every artistic taste and budget.

** ShenArtsFest will take place rain or shine.

First Friday and Old Town Spirit

First Fridays are back! Every first Friday of the month [weather permitting], we host local artists, live music, sip & stroll, special events, and more in the heart of Old Town Winchester.

From 5-9 PM, you can expect a casual and laid-back event atmosphere while our special open container license, Old Town Spirit, is in effect.

This means you can purchase an adult beverage at any participating restaurant, bar, or brewery on the Pedestrian Mall or Boscawen St. and take it with you to walk around, enjoy the music, or even drop in to your favorite retail stores to sip while you shop.

Local favorites Raised on Analog will be at the Taylor Pavilion from 6:30 – 8:30 PM playing all your favorite ’80s hits!

The Shenandoah Valley Discovery Museum also offers free admission on First Friday, from 5-7pm.

First Friday in Old Town

Our November First Friday will get you in the Holiday spirit! Local artists will be set up throughout Old Town Winchester live painting and selling art. Please come and support our local businesses and artists. Big thanks to Other Side of the Tracks Art and Winchester Main Street Foundation for partnering with Old Town Winchester Business Association.

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.

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.

Haunted History Ghost Tour

Prepare yourself for a spine-tingling tour that delves into the mysterious history of Winchester!

Learn of the restless spirits from the Colonial and Civil War eras often seen and heard in the streets and historic buildings of Old Town. Your expert guide weaves a tale of carefully researched history and true ghost stories that will leave you intrigued and hopefully convinced that they are here!

Tour lasts approximately one hour.

Tickets must be purchased in advance at the Winchester-Frederick County Visitors Center, 1400 S. Pleasant Valley Road, Winchester, starting September 11.

Cost: $10
Cash or check only.

Limit of 15 participants per tour.

Call (540) 542-1326 for more information.

In the event of rain, the tour may be canceled. Participants may have the opportunity of attending on one of the other dates, or receive a refund.

Tour is offered Saturday, October 28, Monday, October 30, and Tuesday, October 31 at 6pm.

Meet at the intersection of Cork Street and the Loudoun Street Mall, in the area of the archway.

For more information

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

Winchester Restaurant Week

Love to eat? Restaurant Week provides the opportunity for you to try special menu items prepared by local chefs at each location.

Participating restaurants in Winchester will be offering multi-course menus, meal deals, or discounted pricing.
Take this as an opportunity to dine at some of your favorite restaurants, plus try out ones you’ve never been to before – but always wanted to go.

Takeout is also available for Restaurant Week.

Participating Restaurants include:
Antojitos Mexicanos (Participating Monday – Saturday)
Big L’s Bagels (Participating Monday – Saturday)
Bonnie Blue Southern Market and Bakery (Participating Monday – Saturday)
Cork Street Tavern (Participating Monday – Saturday)
Hideaway Café (Participating Thursday – Saturday)
Island Delights Caribbean Restaurant (Participating Tuesday – Thursday)
Kasbah (Participating Thursday – Saturday)
Knead Bread (Participating Monday – Saturday) 10% Off
KV Kabob (Participating Monday – Saturday)
Sexi Mexi Burrito Bar (Participating Monday – Saturday)
The Wine Room at Taylor Pavilion (Participating Monday – Saturday)
Union Jack Pub and Restaurant (Participating Tuesday – Saturday)
Uno Pizzeria & Grill (Participating Monday – Saturday)
Water Street Kitchen (Participating Monday – Saturday)
Veterans Subs (Participating Monday – Saturday) Menu
Vibrissa Beer and Kitchen (Participating Monday – Saturday)
Violino Ristorante Italiano (Participating Tuesday – Saturday)
Village Square Restaurant (Participating Monday – Saturday)
Willie Sutton’s (Participating Monday – Saturday)

Check out the website for more information and menus! Please check with individual restaurants for reservations.