Why Winter's Better In Leesburg: Beat The Blues With These Local Picks

Winter may be here, but the fun doesn’t slow down in Leesburg. From family outings to seasonal events and easy day trips, there’s plenty around town to keep your calendar full. Just remember to double-check hours, weather updates and ticket details before heading out. And if you want even more local winter ideas, keep scrolling — you’ll find a way to get personalized suggestions based on what you love to do.

ION International Training Center

Address: 19201 Compass Creek Pkwy, Leesburg, VA 20175
Phone: (703) 951-0050
Details: ION International Training Center features twin ice rinks offering public skating, Learn to Skate classes, hockey, figure skating and curling, along with community events throughout the winter. Public skating sessions can sell out, so arriving early is recommended. See the website for the current week’s public skating schedule and pricing.

Inside Ski Training Center

Address: 34-B Catoctin Cir SE, Leesburg, VA 20175
Phone: (571) 707-8873
Details: Inside Ski Training Center uses a revolving ski surface to simulate downhill skiing in a controlled indoor environment. Sessions are tailored to all skill levels, from first-timers to advanced skiers. View available packages and pricing here.

Tally Ho Theater

Address: 19 W Market St, Leesburg, VA 20176
Phone: (703) 777-1665
Details: This restored art deco theater hosts live music, comedy shows and family-friendly performances throughout the winter. Programming includes touring musicians and special events for all ages. Browse upcoming shows and tickets on the Tally Ho Theater website.

Stone Tower Winery

Address: 19925 Hogback Mountain Rd, Leesburg, VA 20175
Phone: (703) 777-2797
Details: Stone Tower Winery offers wine tastings, self-guided vineyard walks and seasonal experiences across its scenic hillside property. Two tasting rooms and curated tours make it a popular winter destination for relaxed indoor-outdoor visits. Learn more about tasting options and tours here.

Wonder Childhood Discovery

Address: 16 W Market St #1, Leesburg, VA 20176
Phone: (703) 857-3432
Details: Wonder is a curated indoor and outdoor play space designed to inspire creativity, curiosity and problem-solving through hands-on play. Admission includes a two-hour indoor play session, with outdoor play available, weather permitting. Book admission online and review visitor guidelines before arriving.

DMV Art Studio

Address: 22611 Markey Ct, Unit 105-B, Second Floor, Sterling, VA 20166
Phone: (301) 804-8562
Details: DMV Art Studio offers hands-on creative workshops including mosaic lamp making, rug tufting and other art projects. It’s a cozy indoor option for date nights, group outings or solo creativity. Reserve a workshop through the studio’s online booking page.

Vanish Farmwoods Brewery

Address: 42245 Black Hops Ln, Leesburg, VA 20176
Phone: (703) 779-7407
Details: Set on 63 acres of fields and forest, Vanish Farmwoods Brewery offers a relaxed taproom experience with locally crafted beers. Indoor seating and seasonal outdoor areas make it a popular winter stop. See the website for current hours and events.

Lucky Strike Leesburg

Address: 1602 Village Market Blvd, Ste 100, Leesburg, VA 20175
Phone: (703) 443-8001
Details: Lucky Strike Leesburg combines upscale bowling with an arcade, casual dining and a full bar. Online lane reservations are available and recommended, especially on weekends. Reserve your lane and explore amenities here.

Want ideas that fit your family and your budget? Enter your ZIP code and preferences — kid-friendly, outdoor, educational and more — for winter getaway recommendations made for you.

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