Plan My Trip

A Winter Weekend of Hikes, Bites, and B&Bs

Pizzoco Pizza Parlor

501 N Loudoun St, Winchester, VA 22601, USA

Mountain Trails

115 N Loudoun St, Winchester, VA 22601, USA

Bells Fine Clothing

122 North Loudoun Street, Winchester, Virginia 22601, USA

Incredible Flying Objects

111 North Loudoun Street, Winchester, VA, USA

Tin Top Art & Handmade

130 North Loudoun Street, Old Town, Winchester, VA, USA

Sweet Basil Thai Cuisine

24 West Main Street, Berryville, VA, USA

Homespun By Smith Meadows

20 West Main Street, Berryville, Virginia 22611, USA

Waypoint House B&B

211 S Church St, Berryville, VA, USA

L'Auberge Provencale

13630 Lord Fairfax Hwy, White Post, VA 22663, USA

Escape into Virginia’s forests and national parks to experience our mountain trails in the serenity of winter. This is one of the best times of year to truly get away from it all. Read on for recommendations and book a two-night hiking getaway in the Valley!

Day 1: Winchester, Clarke County



Start your trip by fueling up with lunch at Pizzoco Pizza Parlor. Pizza lovers will love this local gem. Pizzoco offers fresh pizza made from scratch and cooked in their “old school” deck oven. Enjoy one of their seven house pizzas, including the “Hiker’s Special” (pepperoni, sausage, mushroom, red onion, green pepper), or make your own custom pizza. Pizzoco is the perfect spot to start your day.


Photo Courtesy of Mountain Trails


After lunch, head just a few streets away to pick up any last-minute hiking gear at Mountain Trails camping and hiking store. Their 4,000 sq ft building is packed with everything you need for your next adventure. Mountain Trails carries over 100 brands of the highest quality, including Patagonia, The North Face, Marmot, Howler Bros, and more!




If you’re a shopping lover, check out some other shops while you’re in town like:

  • Bell’s Fine Clothing: Bell’s Fine Clothing has been in business for 91 years, offering high-quality fine clothing for men and women in downtown Winchester. 
  • Incredible Flying Objects: Perfect for those traveling with kids, this shop offers kites, disc golf, darts, toys and novelties. 
  • Tin Top Art & Handmade: Tin Top is a gallery and gift shop located in Winchester, VA featuring carefully curated fine art, jewelry, home goods, cards, clothing and more by independent artists and crafters.


Photo Courtesy of AllTrails


After fueling up and grabbing some last minute supplies, it’s time to start hiking! Head 30 minutes south east towards Bluemont and check out Buzzard Hill via the Appalachian Trail. Buzzard Hill is a 3.4 mile out and back trail that features a stream crossing, two ridge climbs, a unique waterfall, and ruins. 




It is important to keep in mind that it is also hunting season in Virginia from November 29 – January 1. Recommended trails (like this one!) are not on designated hunting land, but please make sure you are aware of your surroundings! 


Photo Courtesy of Sweet Basil Thai Cuisine


After hiking, warm up with a delicious dinner at Sweet Basil Thai Cuisine in downtown Berryville, just 16 minutes away. Sweet Basil Thai is locally owned and offers home-style thai cooking with delicious options like Pad Thai, Pad See Ewe, Pineapple Fried Rice, and Roasted Duck Noodle Soup. 




Looking for a different option? Check out the new Homespun by Smith Meadows, right on Main Street in downtown Berryville. This recently opened restaurant offers farm to table signature hotdogs, paninis, and icecream. 


Photo Courtesy of WayPoint House B&B


When you’re ready to rest for the night, take a short walk and checkin to Waypoint House B&B. This pet-friendly bed and breakfast in downtown Berryville has limited capacity. Ask for the “Traveler’s Retreat”, which features a large room, a spacious en suite bathroom, and beautiful views of the town. 




Looking for another unique bed & breakfast experience? Check out L’Auberge Provencale Bed and Breakfast for an authentic Provençale experience in a romantic B&B, with gracious service and luxurious guest rooms. This stay is just a few miles away.

Day 2: Clarke County, Warren County


Photo Courtesy of Cordial Coffee Co. 


After a restful night of sleep, enjoy breakfast at your B&B or venture out to explore more of Berryville. Cordial Coffee is a special coffee roastery and cafe that offers hand-poured coffees, traditional espresso beverages, quality loose-leaf teas, real-fruit smoothies, and made-to-order gluten free waffles.


While in town, check out some of Berryville’s shops:


Photo Courtesy of Alltrails – Snead Farm


Once you’re caffeinated and ready to explore, head to a day at Snead Farm Dickey Ridge Loop Trail. Snead Farm Dickey Ridge Loop Trail is a 3.4 mile loop trail in the Shenandoah National Park located near Front Royal, Virginia. This trail features a beautiful overlook that makes the uphill climb worth it! 




Looking for an easier trail for the whole family? Check out Cool Springs Battlefield for a more accessible walk. This 2.7 mile loop is paved and features interesting historical signage and passes by the Shenandoah River and a waterfall.


Photo Courtesy of Vibrissa Beer



After a great hike, head to Vibrissa Beer in downtown Front Royal for a delicious lunch and a well-deserved beer! Vibrissa Beer, formerly known as Front Royal Brewing Company, features Pilsners to edgy Sours and Hazy IPAs. Vibrissa has a craft beer style for everyone. 




If you’d like to stay a second night in the area and want to switch it up, check out this luxury cabin, just a 10-minute drive from Front Royal. Amenities include a beautiful mountain view with a firefit, river access, and over 20 acres to explore!


Looking for even more in the Shenandoah Valley? Head to Winchester, Clarke County, and Warren County online and book your trip today!


one of the most popular

getaway destinations in Virginia