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Savor the Season: Winter Food and Drink Festivals in Shenandoah Valley

Writer's picture: Casey WoodburnCasey Woodburn

Winter in the Shenandoah Valley isn’t just about picturesque snow-covered landscapes and cozy getaways. It’s also the season to indulge your taste buds at some of the region’s most delightful food and drink festivals. From hearty comfort foods to warming winter beverages, here are the top festivals you won’t want to miss this season.


Festive Food and Beverage Delights Cocktails
Festive Food and Beverage Delights Cocktails

1. Virginia Wine & Craft Festival
Chester Street Tavern 
Chester Street Tavern 

Celebrate the best of Virginia’s winemaking and craft industries at this annual winter gathering. Sample wines from local vineyards, savor artisan foods, and explore handmade crafts while enjoying live music.


Here's what you can expect at the festival:
  • Wine, Cider & Mead Tastings: Sample wines from various Virginia wineries along with cider and mead from local breweries.

  • Arts & Crafts: Browse unique creations from local artists and crafters, including jewelry, pottery, paintings, and more.

  • Food & Beverages: Enjoy delicious food from local vendors, including everything from BBQ and pizza to funnel cakes and ice cream.

  • Live Entertainment: Enjoy live music throughout the day from a variety of talented bands and musicians.

  • Family Fun: Kids will enjoy activities like face painting and balloon animals.


    🌐 Learn More Here


Tip: Dress warmly as some activities take place outdoors.


2. Winter Brews & Blues Festival


The Steel Wheels w/ special guest Driftwood
The Steel Wheels w/ special guest Driftwood

Pair the best local craft beers with the soulful sounds of live blues music. This festival is a cozy indoor escape featuring brewery showcases, delicious food vendors, and unforgettable performances.



Pro Tip: Arrive early to grab a prime seat for the live performances.


3. Comfort Food & Cider Fest

Indoor Winter Farmers Market
Indoor Winter Farmers Market

A community-centered event that provides a cozy venue for local farmers, artisans, and producers to showcase their goods during the colder months. It typically runs weekly, offering a warm and welcoming space for residents and visitors to connect with the region's best locally sourced products.



Tip: Don’t miss the chance to sample freshly baked goods paired with local honey or jams, often made from ingredients sourced right in the Shenandoah Valley.


4. Chocolate Lovers’ Weekend

2025 CHOCOLATE LOVERS FESTIVAL
2025 CHOCOLATE LOVERS FESTIVAL

Indulge in all things chocolate at this sweet winter festival. From chocolate tastings and pairings to creative chocolate-infused dishes, this event is a must for dessert enthusiasts.



Pro Tip: Many vendors offer exclusive Valentine’s Day specials, so it’s a great opportunity for early gift shopping.


5. Valley Winter Feast


Winter Wine Weekend
Winter Wine Weekend

This farm-to-table celebration highlights the valley’s winter harvest. Enjoy multi-course meals crafted by local chefs using fresh, seasonal ingredients sourced from nearby farms.



Tip: Make reservations early as these exclusive dinners often sell out.


Make It a Weekend Getaway

Turn your festival visit into a winter retreat by staying in one of the valley’s charming accommodations:

Extend Your Culinary Adventure: Where to Stay

Turn your festival visits into a winter retreat by staying in one of the valley’s charming accommodations. With options close to each event, you can enjoy the best of the Shenandoah Valley’s culinary and cultural experiences.


Why Stay in the Valley?

  • Proximity to festival locations.

  • Cozy and unique lodgings perfect for families, couples, or solo travelers.

  • Opportunities to explore local food scenes, wineries, and breweries.



Capture and Share Your Shenandoah Foodie Adventures

Your Shenandoah Valley adventure deserves to be shared! Tag us in your photos for a chance to be featured:


Plan Your Visit Today

Winter food and drink festivals in the Shenandoah Valley are the perfect way to savor the season while supporting local artisans and businesses. From indulgent chocolate to farm-fresh feasts, these events promise a taste of Shenandoah you won’t forget.


🌐 Plan Your Culinary Adventure Here: Visit Shenandoah Valley


Immerse yourself in the festive spirit of the Shenandoah Valley this season. Every bite and sip is rich with local flavors, tradition, and the warmth of community. Bring your appetite and get ready to celebrate the flavors of winter in the valley!


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