Winchester Christmas 2025

What to Expect This Christmas in Winchester!

Enjoy the festive season in Winchester with our ultimate holiday guide. Whether you're rediscovering your city or seeing it for the first time, this guide brings you the best of Winchester's festive season. One highlight is the Winchester Old Town Winter Village, where charming wooden huts offer unique gifts, delightful treats, and a warm atmosphere for all ages. With a variety of local vendors and festive entertainment, it captures the spirit of the season. Another key event is the Christmas Maker’s Market, showcasing handmade crafts and special holiday goodies that celebrate local artisans. And the Boyce Volunteer Fire and Rescue Company's Fall Bazaar and Craft Show is something you definitely don't want to miss, featuring a variety of crafted items and community spirit. See more details on these and other fun events and activities below!

Find the best Christmas events in Winchester this year!

Winchester Christmas Events

Winchester Christmas Markets and Shopping (2)

The Fall Bazaar 2025 in Boyce

Details

📍 Boyce, VA, US

(8.5 mi from Winchester)

The Fall Bazaar 2025

Local artists and crafters offering unique holiday gifts.

When

Saturday, October 25, 2025

Event Details

📷 Photo Friendly: 📷📷📷📷📷

💰 Budget: FREE

🎄 Family Friendly: 🎄🎄🎄🎄🎄

⚡ Energy: Low

Event Description

Get a head start on your holiday shopping at The Fall Bazaar 2025. This event brings together local artists and crafters to offer unique, handmade gifts. Discover everything from wreaths and jewelry to pottery and handmade paper, ensuring you find the most distinctive presents for your loved ones.

More

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⭐ Best For: Holiday shopping, supporting local artisans

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Holiday Handmade Market in Ranson

Details

📍 Ranson, WV, US

(17.6 mi from Winchester)

Holiday Handmade Market

Over 90 vendors at two holiday market locations

When

Friday, November 21, 2025

Event Details

📷 Photo Friendly: 📷📷📷📷📷

💰 Budget: FREE

🎄 Family Friendly: 🎄🎄🎄🎄🎄

⚡ Energy: Moderate

Event Description

Discover a festive holiday shopping experience at the Holiday Handmade Market. Browse unique, handcrafted gifts from over 90 local artisans across two vibrant locations in Ranson and Bolivar. Find the perfect presents and soak in the seasonal cheer.

More

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⭐ Best For: Holiday shopping, unique gifts, local artisans

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Near Winchester

Leesburg Christmas Events

Crush With Us Grape Stomping in Bluemont

Bluemont

Details

Crush With Us Grape Stomping

Annual grape stomping experience with keepsake creation.

📷📷📷📷📷 💰 $$ 🎄🎄🎄🎄🎄

📏 18.6 miles from Winchester

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Christmas Village at Leesburg Animal Park in Leesburg

Leesburg

Details

Christmas Village at Leesburg Animal Park

Christmas Village with animal encounters and Santa visits

📷📷📷📷📷 💰 $$ 🎄🎄🎄🎄🎄

📏 31.4 miles from Winchester

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See all 4 events in Leesburg →

Hagerstown Christmas Events

Hagerstown Winter Craft and Vendor Event in Hagerstown

Hagerstown

Details

Hagerstown Winter Craft and Vendor Event

Winter craft and vendor event with diverse artisans

📷📷📷📷📷 💰 $ 🎄🎄🎄🎄🎄

📏 36.9 miles from Winchester

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Christ Kindl Markt Hagerstown in Hagerstown

Hagerstown

Details

Christ Kindl Markt Hagerstown

Traditional German Christmas market with artisan vendors and local food.

📷📷📷📷📷 💰 $ 🎄🎄🎄🎄🎄

📏 38.3 miles from Winchester

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See all 8 events in Hagerstown →

South Riding Christmas Events

Dickens of a Christmas in Middleburg in Middleburg

Middleburg

Details

Dickens of a Christmas in Middleburg

Town transformed into a Charles Dickens novel scene

📷📷📷📷📷 💰 $$ 🎄🎄🎄🎄🎄

📏 27.3 miles from Winchester

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Christmas in Middleburg in Middleburg

Middleburg

Details

Christmas in Middleburg

A charming small-town Christmas celebration with a renowned parade.

📷📷📷📷📷 💰 $$ 🎄🎄🎄🎄🎄

📏 27.4 miles from Winchester

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Linton Hall Christmas Events

Haymarket Christmas and Holiday Celebration in Haymarket

Haymarket

Details

Haymarket Christmas and Holiday Celebration

Christmas craft bazaar with local artisans

📷📷📷📷📷 🎄🎄🎄🎄🎄

📏 38.3 miles from Winchester

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Frederick Christmas Events

Myersville Holiday Farmers Market in Myersville

Myersville

Details

Myersville Holiday Farmers Market

Year-round farmers market with seasonal indoor and outdoor offerings.

📷📷📷📷📷 💰 $ 🎄🎄🎄🎄🎄

📏 38.9 miles from Winchester

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A Motown Christmas in Frederick

Frederick

Details

A Motown Christmas

Motown-infused holiday music performance

📷📷📷📷📷 💰 $$ 🎄🎄🎄🎄🎄

📏 43.2 miles from Winchester

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See all 4 events in Frederick →

Chantilly Christmas Events

Capital Art and Craft Festivals - Winter Market in Chantilly

Chantilly

Details

Capital Art and Craft Festivals - Winter Market

Over 300 juried artists showcasing handmade art and crafts.

📷📷📷📷📷 💰 $$ 🎄🎄🎄🎄🎄

📏 43.9 miles from Winchester

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Northern Virginia Christmas Market in Chantilly

Chantilly

Details

Northern Virginia Christmas Market

Over 300 fine artisans and unique Christmas collectibles.

📷📷📷📷📷 💰 $ 🎄🎄🎄🎄🎄

📏 43.9 miles from Winchester

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Herndon Christmas Events

Holiday Arts and Crafts Show in Herndon

Herndon

Details

Holiday Arts and Crafts Show

Over 80 local and regional vendors with handmade goods.

📷📷📷📷📷 💰 FREE 🎄🎄🎄🎄🎄

📏 43.8 miles from Winchester

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Herndon WinterMarkt in Herndon

Herndon

Details

Herndon WinterMarkt

European-style Christmas market in historic Herndon

📷📷📷📷📷 💰 $ 🎄🎄🎄🎄🎄

📏 44.2 miles from Winchester

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Oak Hill Christmas Events

Frying Pan Farm Park Holiday Lights in Herndon

Herndon

Details

Frying Pan Farm Park Holiday Lights

Historic farm transformed by holiday lights

📷📷📷📷📷 💰 FREE 🎄🎄🎄🎄🎄

📏 44.2 miles from Winchester

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Cumberland Christmas Events

Breakfast with Santa at Mezzos in Cumberland

Cumberland

Details

Breakfast with Santa at Mezzos

Breakfast with Santa Claus

📷📷📷📷📷 💰 $$ 🎄🎄🎄🎄🎄

📏 45.2 miles from Winchester

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The Polar Express Train Ride in Cumberland

Cumberland

Details

The Polar Express Train Ride

Immersive Polar Express train journey with Santa visit.

📷📷📷📷📷 💰 $$ 🎄🎄🎄🎄🎄

📏 45.3 miles from Winchester

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See all 3 events in Cumberland →

Manassas Christmas Events

American Festival Pops Orchestra Holiday Pops: Songs of the Season in Manassas

Manassas

Details

American Festival Pops Orchestra Holiday Pops: Songs of the Season

Annual holiday concert by the American Festival Pops Orchestra.

📷📷📷📷📷 💰 $$ 🎄🎄🎄🎄🎄

📏 45.2 miles from Winchester

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Bull Run Festival of Lights in Centreville

Centreville

Details

Bull Run Festival of Lights

2.5-mile drive-through holiday light display

📷📷📷📷📷 💰 $$ 🎄🎄🎄🎄🎄

📏 45.3 miles from Winchester

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Last updated: 10/9/2025