Have a holly-jolly Christmas with Winchester’s holiday events

Make your list and check it twice for some fantastic, festive holiday events taking place in Winchester – everything from open house merriment to farmers market fun.

“Put us on your list of holiday must-dos,” said Bailey Milheiser, manager of Beech Springs Farmers Market.

“Our Christmas Market is a great way to meet all kinds of local artists and crafters all in one place,” she said. “We think it gets everyone in the holiday spirit – and that it’s a great way to shop Small Business Saturday!”

  • Downtown Holiday Open House, Nov. 3, 4, 5, 6. Extended hours. Only 51 days left until Christmas, but don’t despair! Winchester’s got your back. Enjoy a full-on holiday atmosphere in the Historic Downtown District, with storefronts trimmed in garland and seasonal displays and shops opening their doors with extended hours, holiday snacks and treats, special sales and discounts and more holiday shopping fun than you can shake a Christmas stocking at. Stroll up and down Main Street – and in Winchester, it really is up and down with its elevated sidewalk – popping into a variety of locally-owned shops. 
  • Leeds Center for the Arts presents “Newsies JR,” Nov. 4-6 and 11-13, 7:30 p.m. Fridays and Saturdays and 2:30 p.m. Sundays. When powerful newspaper publishers raise prices at the newsboys’ expense, the charismatic Jack Kelly rallies newsies from across the city to strike against the unfair conditions. Inspired by the rousing true story of newsboys in turn-of-the-century New York City, Newsies JR. features a Tony Award-winning score by Alan Menken and Jack Feldman and a book by Tony Award winner Harvey Fierstein. With high-energy song and dance numbers performed by an incredible cast of young performers, this is a show you don’t want to miss! Tickets here.
  • Small Business Saturday, Nov. 26, 10 a.m.-5 p.m. Skip overcrowded malls and mass market merch for thoughtful, curated gift items from the shops in Winchester’s Historic Downtown District. Find original pottery pieces at Dirty South Pottery, one-of-a-kind artworks – watercolors, needlework, wood crafts – from Arts on Main Gallery, the perfect hostess gift at The Craft Nook and so much more. Fuel up at one of Winchester’s downtown restaurants – pizza from La Trattoria, a slice of sugar cookie cheesecake from Cheesecake & Company – and know you are helping support locally owned small businesses, which help support the local economy.
  • Beech Springs Christmas Market: Nov. 26, 10 a.m.-4 p.m. Free. Sip and shop, browse and buy from more than 60 local vendors, including Creative Coffees, Abettor Brewery, Harkness Edwards Winery and dozens more. Queue up for hot, juicy burgers from Bell on Wheels Food Truck and some sweet treats from Cookies and Cream. Enjoy live holiday music throughout the day, with Eli Holbrook on piano and Izzie and Erin Smith singing and playing guitar. Parking is available in several nearby lots, including Forest Grove Christian Church and JK’s Café.
  • Old Fashion Christmas Parade, 6 p.m. Dec. 3. Can there be a more Christmassy outing than a holiday parade through a small town’s downtown? With friends and neighbors gathered along the sidewalks, gliding floats and marching bands, lampposts all aglow and everyone awaiting the appearance of Santa Claus? Join us for this most wonderful time of the year.
  • Jingle & Mingle, Downtown Main Street, all-day, Dec. 8-11. Come shop-hop in Winchester’s Historic District, home to locally-owned shops, boutiques and restaurants for festive finds for holiday gift giving.