The 3rd Annual Chocolate Escape returns to Old Town on Saturday, February 6, 2016 from 2 p.m. to 5 p.m. 14 Restaurants and over 30 Retail Shops will be participating this year. Click here for details and a list of participants.
Find out more »Once again Old Town Winchester will be honoring Fire and Rescue personnel and their families on Thursday evening July 20th. Those businesses participating in the evening are listed with this posting. Area fire apparatus and antique apparatus will be on display from 6pm – 8pm on the walking mall. Bring a chair and join us at dark on the lawn of the Old Court House where the Winchester Parks and Recreation Department will be showing the Batman Lego Movie. WFRD…
Find out more »Experience the Civil War and so much more! Our walking tours explore many layers of history that make up the fabric of Old Town Winchester! Discover more about the citizens and the events that took place here in Winchester and the surrounding Shenandoah Valley. Make your reservation by calling 540-542-1326, and meet your guide at 2 N. Cameron Street. $10.00 per person, payable to your guide. May-October, 2018 2nd Fridays at 6pm (no tour Oct. 12) 3rd Saturdays at 10am
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One Mile Road Race on the Loudoun Street in Historic Old Town Winchester, Virginia on Memorial Day. This is the 32nd annual event and will again serve as the RRCA Virginia State Championship race. There will be prize money to the top 5 runners and first masters (equal for men and women): 1st - $500, 2nd - $250, 3rd-$150, 4th - $100, 5th - $75; 1st Masters (40+) - $75. NEW for 2019: we are moving the 12-14 year age…
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The City of Winchester and Winchester Fire & Rescue Department will be hosting Fire and Rescue Appreciation Day on Thursday, July 18. It will include EMS and Fire vehicles for children to “Tour a Truck” and end with the How to Train Your Dragon: The Hidden World movie at dusk at the Taylor Pavilion. All activities are free. Participating downtown businesses will offer a special discount or promotion that day for Fire & Rescue personnel. Businesses include: Aroma Deli 201 E. Boscawen Street…
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The community is invited to meet and interact with Winchester Police officers as well as community partners and crime prevention groups such as the Winchester City Sheriff’s Office and Winchester Fire & Rescue. The WPD Bike Team, SWAT team, and Volunteers in Policing will provide educational demonstrations and services for neighborhood and child safety. Enjoy free food, live music, and children’s activities. Bring seating and stay a while! Metered parking in the downtown area is free after 6 p.m.
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The annual Old Town Winchester Oktoberfest presented by Compass West Realty returns on October 11-12. Attendees will have the opportunity to enjoy German inspired beer and food while experiencing sights, sounds and traditions of Oktoberfest. This event happens throughout Old Town Winchester, including the Loudoun Street Mall, historic Taylor Pavilion and the 1840 Courthouse lawn. NEW THIS YEAR: Keg tapping ceremony with Austrian horses! The public is invited to join Austrian Haflinger horses, Yeager and Meister, in a procession beginning near cork…
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We’ve got a holly jolly mystery on our hands, folks! Ever since we put our tree up, more decorations just keep springing up overnight. There’s lights on our trees, bows and bells on our streets, why—the Taylor Pavilion’s even got a big wreath! Some sort of magic is afoot in Old Town…so why not bring the whole family down? We have it on good authority that some of Santa’s own staff are going to finish up their work this Friday…
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Old Town Winchester kicks off the 2022 event season with the return of an annual favorite, Chocolate Escape! Join us on Saturday, February 5 for a decadent day out enjoying all the chocolate-covered delights that our restaurants and retailers have to offer, and find those sweet Valentine treats you’re looking for! For more information, visit enjoyotw.com or find us on Facebook and instagram at @oldtownwinchesterva ! From 2-5 PM, participating retailers will be offering sweet deals, discounts, or samples, while…
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On the first Friday of every month, Old Town Winchester becomes an immersive gallery where visitors to the historic business district can shop, dine, and stroll while taking in local art, live music, and artisan crafts. Artists will be on-site to show their works and wares, and free open air concerts at the Taylor Pavilion make this the perfect chance to come down and experience all that Old Town has to offer! Old Town Spirit will be in effect…
Find out more »On the first Friday of every month, Old Town Winchester becomes an immersive gallery where visitors to the historic business district can shop, dine, and stroll while taking in local art, live music, and artisan crafts. Artists will be on-site to show their works and wares, and free open air concerts at the Taylor Pavilion make this the perfect chance to come down and experience all that Old Town has to offer! Old Town Spirit will be in effect…
Find out more »On the first Friday of every month, Old Town Winchester becomes an immersive gallery where visitors to the historic business district can shop, dine, and stroll while taking in local art, live music, and artisan crafts. Artists will be on-site to show their works and wares, and free open air concerts at the Taylor Pavilion make this the perfect chance to come down and experience all that Old Town has to offer! Old Town Spirit will be in effect…
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Waldo's Back and up to his shenanigans! He's been spotted around many of our local downtown businesses! Grab a Passport at Winchester Book Gallery to see where he's hiding. Spot Waldo and get your Passport stamped at each shop. Find 25 of the Waldos to be entered in a prize drawing!
Find out more »On the first Friday of every month, Old Town Winchester becomes an immersive gallery where visitors to the historic business district can shop, dine, and stroll while taking in local art, live music, and artisan crafts. Artists will be on-site to show their works and wares, and free open air concerts at the Taylor Pavilion make this the perfect chance to come down and experience all that Old Town has to offer! Old Town Spirit will be in effect…
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It's almost time for Rockin' Independence Eve! Join us in Old Town Winchester on Sunday, July 3 for the return of an old favorite. We'll have Old Town Spirit in effect from 2-10 PM so you can take full advantage of all the food and drink that Loudoun and Boscawen Street have to offer. Hometown favorites RTG hit the Taylor Pavilion stage at 4 PM, then we invite you to take a dinner break until 7 PM when the Texas…
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KidzFest will return this year! This free, family-friendly event features exhibits highlighting education, art, music, and more! Some of this year's activities include: Library card sign-ups with Handley Library Creating origami animals with the Museum of the Shenandoah Valley Making and decorating paper fans with the Youth Development Center Giant chess and other challenge activities with Shenandoah Valley Chess Club Trial classes with Armstrong Irish Dance Academy Dance demonstrations from Dance Ambassadors Art activities with Arte Libre Susie the Clown 12-4pm…
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It's been a long month of finding Waldo! Today will be out grand celebration! 1pm at the Winchester Book Gallery, we will be hosting a party and a prize drawing. You'll be entered in the prize drawing if you have found at least 25 out of 48 Waldos AND brought your passport back to the Winchester Book Gallery! Best of luck to all!
Find out more »On the first Friday of every month, Old Town Winchester becomes an immersive gallery where visitors to the historic business district can shop, dine, and stroll while taking in local art, live music, and artisan crafts. Artists will be on-site to show their works and wares, and free open air concerts at the Taylor Pavilion make this the perfect chance to come down and experience all that Old Town has to offer! Old Town Spirit will be in effect…
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Old Town Winchester will present the FIDDLES & FIFTHS FESTIVAL this August featuring headliner performances by acclaimed African-American string band EBONY HILLBILLIES and celebrated New Jersey septet RAILROAD EARTH. The festival, which also features local act DUNLAP & MABE, Maryland-based LOW RIVER EXPRESS, and Richmond’s THE HASHBURY COLLECTIVE, is a brand-new two-day event celebrating bluegrass, bourbon, and the great businesses and atmosphere of Old Town Winchester! All mainstage performances are free to the public. Other additions to the festival will…
Find out more »On the first Friday of every month, Old Town Winchester becomes an immersive gallery where visitors to the historic business district can shop, dine, and stroll while taking in local art, live music, and artisan crafts. Artists will be on-site to show their works and wares, and free open air concerts at the Taylor Pavilion make this the perfect chance to come down and experience all that Old Town has to offer! Old Town Spirit will be in effect…
Find out more »On the first Friday of every month, Old Town Winchester becomes an immersive gallery where visitors to the historic business district can shop, dine, and stroll while taking in local art, live music, and artisan crafts. Artists will be on-site to show their works and wares, and free open air concerts at the Taylor Pavilion make this the perfect chance to come down and experience all that Old Town has to offer! Old Town Spirit will be in effect…
Find out more »On the first Friday of every month, Old Town Winchester becomes an immersive gallery where visitors to the historic business district can shop, dine, and stroll while taking in local art, live music, and artisan crafts. Artists will be on-site to show their works and wares, and free open air concerts at the Taylor Pavilion make this the perfect chance to come down and experience all that Old Town has to offer! Old Town Spirit will be in effect…
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The Apparition Trail returns to Old Town for Thanksgiving Weekend! Join host JP Murphy on a walking tour exploring haunts and history in the ghostliest time of year. Tour meets at John Handley Library, 100 W Piccadilly St. Call 540-533-9942 for details. Friday 11/25-tours at 7p and 915p Saturday 11/26-7p and 915p Sunday 11/27 through 12/1 at 7p. $15 per person, kids 12 and under free. Cash only.
Find out more »The Apparition Trail returns to Old Town for Thanksgiving Weekend! Join host JP Murphy on a walking tour exploring haunts and history in the ghostliest time of year. Tour meets at John Handley Library, 100 W Piccadilly St. Call 540-533-9942 for details. Friday 11/25-tours at 7p and 915p Saturday 11/26-7p and 915p Sunday 11/27 through 12/1 at 7p. $15 per person, kids 12 and under free. Cash only.
Find out more »The Apparition Trail returns to Old Town for Thanksgiving Weekend! Join host JP Murphy on a walking tour exploring haunts and history in the ghostliest time of year. Tour meets at John Handley Library, 100 W Piccadilly St. Call 540-533-9942 for details. Friday 11/25-tours at 7p and 915p Saturday 11/26-7p and 915p Sunday 11/27 through 12/1 at 7p. $15 per person, kids 12 and under free. Cash only.
Find out more »The Apparition Trail returns to Old Town for Thanksgiving Weekend! Join host JP Murphy on a walking tour exploring haunts and history in the ghostliest time of year. Tour meets at John Handley Library, 100 W Piccadilly St. Call 540-533-9942 for details. Friday 11/25-tours at 7p and 915p Saturday 11/26-7p and 915p Sunday 11/27 through 12/1 at 7p. $15 per person, kids 12 and under free. Cash only.
Find out more »The Apparition Trail returns to Old Town for Thanksgiving Weekend! Join host JP Murphy on a walking tour exploring haunts and history in the ghostliest time of year. Tour meets at John Handley Library, 100 W Piccadilly St. Call 540-533-9942 for details. Friday 11/25-tours at 7p and 915p Saturday 11/26-7p and 915p Sunday 11/27 through 12/1 at 7p. $15 per person, kids 12 and under free. Cash only.
Find out more »The Apparition Trail returns to Old Town for Thanksgiving Weekend! Join host JP Murphy on a walking tour exploring haunts and history in the ghostliest time of year. Tour meets at John Handley Library, 100 W Piccadilly St. Call 540-533-9942 for details. Friday 11/25-tours at 7p and 915p Saturday 11/26-7p and 915p Sunday 11/27 through 12/1 at 7p. $15 per person, kids 12 and under free. Cash only.
Find out more »The Apparition Trail returns to Old Town for Thanksgiving Weekend! Join host JP Murphy on a walking tour exploring haunts and history in the ghostliest time of year. Tour meets at John Handley Library, 100 W Piccadilly St. Call 540-533-9942 for details. Friday 11/25-tours at 7p and 915p Saturday 11/26-7p and 915p Sunday 11/27 through 12/1 at 7p. $15 per person, kids 12 and under free. Cash only.
Find out more »The Apparition Trail returns to Old Town for Thanksgiving Weekend! Join host JP Murphy on a walking tour exploring haunts and history in the ghostliest time of year. Tour meets at John Handley Library, 100 W Piccadilly St. Call 540-533-9942 for details. Friday 11/25-tours at 7p and 915p Saturday 11/26-7p and 915p Sunday 11/27 through 12/1 at 7p. $15 per person, kids 12 and under free. Cash only.
Find out more »The Apparition Trail returns to Old Town for Thanksgiving Weekend! Join host JP Murphy on a walking tour exploring haunts and history in the ghostliest time of year. Tour meets at John Handley Library, 100 W Piccadilly St. Call 540-533-9942 for details. Friday 11/25-tours at 7p and 915p Saturday 11/26-7p and 915p Sunday 11/27 through 12/1 at 7p. $15 per person, kids 12 and under free. Cash only.
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ShenArts and Old Town Winchester invite the businesses of Old Town to decorate storefronts and windows for a creative celebration and contest. Submit your best photos on our website by December 10 to be included. The public is invited to visit all the participating merchants, view their festive handiwork, and vote for three favorites based on creativity and curb appeal for the People’s Choice awards. Voting takes place here from December 11-18. Don’t be a grinch, submit now…Happy Holidays from…
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All February long, visit your favorite Old Town businesses to see brand new works of art from local Black artists up on display! We partnered with our friends at Arte Libre VA and Selah Theatre Project to commission new, original works in a celebration of Black culture in Winchester and to turn Old Town into a unique walking gallery all month long. FEATURED ARTISTS: Dustin Walker at Tin Top Art and Handmade Terrance Wilson at The Hideaway Cafe Vonnie Law…
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Get a little extra sweetness in your life with our 10th annual Chocolate Escape! Join us in Old Town from 2-5pm for $5 chocolatey treats offered by our retailers and restaurants. More information coming soon!
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Is spring in the air already? Or is that just the feeling of Celtic Fest, fast approaching? Celtic Fest is back this year for another celebration of all things Irish--and Scottish, Welsh, Breton--you get the idea. Kick off St. Patrick's Day early by visiting Old Town Winchester to explore various venues for food, drink, live music, cultural displays, dancing, retail sales, artisan vendors, and more! Full schedule and list of participants coming soon--in the meantime take a look at this…
Find out more »Back for another year, it’s Fiddles & Fifths in Old Town Winchester! Get ready for an unforgettable weekend as we send off summer with a tribute to the great Appalachian tradition of bluegrass music and the homegrown taste of Virginia bourbon! This returning event takes place in the heart of Old Town and brings a festival atmosphere that’s half world-class music mainstage, half backyard block party with all your local favorites. Headlining this year is Grammy award-winning Nashville phenomenon The…
Find out more »Get ready for the Old Town Winchester Oktoberfest 2023, presented by Katie Moody Homespire Mortgage! This much-anticipated event is organized by and will benefit Literacy Volunteers Winchester Area (LVWA). Mark your calendars for September 29th from 5-10 pm, as we gather in beautiful Old Town Winchester to celebrate Oktoberfest in grand style! Ticket prices will be $30 until the day of the event, and $40 at the gate. Join us for an evening filled with refreshing brews, live entertainment, and…
Find out more »Old Town Winchester merchants on the Loudoun Street Mall will host Old Town Trick or Treat from 2–4 pm!
Find out more »Grab your most creative costumes… It’s time to get spooky with the best craft breweries in town! Proceeds will be donated to the Winchester Area SPCA! Pub crawl participants will enjoy exclusive discounts at each participating brewery during the event. Bring your completed passport to the prize tent located by the stage before 7:30pm to enter the costume contest for a chance to win prizes and gifts to all your favorite locations! How it works: 1. Pick up your brewery…
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Windependent Weekend is a local retail event that focuses on celebrating and supporting our Old Town small businesses. "Put your money where your heart is" by coming out to show love to all the local businesses that make Winchester special!
Find out more »It’s time to get ready for the Holiday Parade in Old Town Winchester! The Holiday Parade will be held Monday, November 27 at 7:00 p.m. with Santa lighting the tree in Old Town immediately after the parade.
Find out more »Be transported to a cozy European holiday market this Christmas season in beautiful, historic Old Town Winchester, Virginia! A village of traditional European food and crafts vendors will be at the heart of the Old Town pedestrian mall, and our many shops will be fully decked out for the holidays and offering specials for shoppers young and old. On Friday, December 8th enjoy a grown-up good time with a 12 Days of Christmas restaurant crawl in the evening to benefit…
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Make your way to Old Town Winchester at 5:00 pm to catch an early New Year's Eve dinner at one of Winchester's fine dining establishments and enjoy an evening full of family-friendly entertainment. FREE parking in all Old Town garages from noon (12:00 pm) Sunday 12/31 through noon (12:00 pm) Monday 1/1! Patrons leaving after 12:00 pm on Monday will have to pay the lost ticket fee of $15. 5:00 - 6:00 pm: James Wood High School Jazz Band performing…
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All February long, visit your favorite Old Town businesses to see brand new works of art from local Black artists up on display! We partnered with our friends at Arte Libre VA to commission new, original works in a celebration of Black culture in Winchester and to turn Old Town into a unique walking gallery all month long. Follow this page for more information on the pieces and the artists behind them!
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Join us in Old Town on Saturday, February 10th from 2–5 PM for our 11th annual Chocolate Escape! For just $5 each you can sample some incredible chocolate confections at our participating restaurants, and many of our merchants will be offering some sweet (literally) giveaways and deals. Our list is growing, so be sure to check back for more delicious offers from our local businesses.
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Join us in Old Town on March 16th from noon to 10 PM to celebrate Winchester's Celtic heritage with food and artisan craft vendors, live entertainment and music, Irish dancing, and more! New this year is a St. Paddy's brewery crawl from 5 to 10 PM, sponsored by our amazing local breweries.
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First Fridays are back! Every first Friday of the month , 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…
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