10 Fun Things to Do During Winter in Virginia

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Winter weather in Virginia varies greatly, depending on whether you’re in the Virginia mountains or along the coast.

But, as longtime VA residents, we generally find the Virginia climate agreeable– not too hot, and not too cold.

So Winter activities in Virginia can run the gamut from snow skiing and snowboarding at mountain resorts to golfing in a nearby valley or taking a sunny stroll on an ocean boardwalk.

Whether you choose a romantic getaway to a luxury spa in the Blue Ridge Mountains or take a Virginia Beach whale watching tour, the Winter months here are chock full of fun! 

Read on for our in-depth guide to 10 fun things to do in Virginia during the Winter, including great options for Christmas, Valentine’s Day, and family-friendly weekend getaways!

READ MORE: The Best Places for Snow Skiing in Virginia

Top Places to Stay in Virginia in the Winter:

  1. The Blackburn Inn & Conference Center (elegant historic Staunton getaway w/ spa)
  2. Holiday Inn Express & Suites(IHG hotel in Staunton w/ good breakfast & indoor pool)
  3. Black Lantern Inn (upscale Roanoke Inn w/ unparalleled breakfast cuisine close to the BRP)
  4. Friendly City Inn B&B (cozy historic Harrisonburg inn w/ delicious breakfast)
  5. Kimpton – The Forum Hotel (boutique Charlottesville Hotel in UVA Darden campus)
  6. Cedars of Williamsburg Bed & Breakfast (historic B&B 10 min walk to Colonial Williamsburg)
  7. Coastal Hotel & Suites (Virginia Beach oceanfront hotel on boardwalk w/ good breakfast)

Things to Do for Winter in Virginia Guide

  1. A Christmas Carol in Staunton VA
  2. Drive The Blue Ridge Parkway
  3. Explore Assateague and Chincoteague Islands
  4. Grand Illumination at Colonial Williamsburg
  5. The Highland County Maple Festival
  6. Hiking on Skyline Drive
  7. Kingsmill Resort in Williamsburg
  8. Romantic Weekend at The Martha Washington
  9. Ski a Virginia Mountain Resort
  10. Virginia Beach Boardwalk and Whale Watching

READ MORE: 20 Things to Do in the Blue Ridge Mountains of Virginia

Blackfriars Playhouse in Staunton VA
Photo courtesy Blackfriars Playhouse 

1. A Christmas Carol in Staunton VA

Near the top of our Virginia Christmas to-do list is “dinner and a show” in the lovely town of Staunton VA. Specifically Charles Dickens’ classic, A Christmas Carol, at the American Shakespeare Center’s Blackfriars Playhouse.

The talented Blackfriars Playhouse stage crew transforms their Staunton VA stage into a slice of Victorian London, where you can watch Ebenezer Scrooge’s dramatic Christmas Eve transformation.

Audiences young and old will be thrilled as the ghosts of Christmas past, present, and future help warm Scrooge’s cold heart, with lots of humor along the way.

Come early to explore the myriad Staunton restaurants and shops, which will all be decorated with holiday flair. For an amazing night, try pairing the play with a stay at Staunton’s grand hotel, Hotel 24 South.

READ MORE: The 10 Best Things to Do in Staunton VA

Virginia's Blue Ridge Parkway in Winter
The Blue Ridge Parkway in Winter

2. Drive the Blue Ridge Parkway

Running 469 miles from Great Smoky Mountains National Park to Shenandoah National Park, the Blue Ridge Parkway is America’s longest linear park, providing an incredible way to see the Blue Ridge Mountains in Winter.

The BRP offers 200+ stunning scenic overlooks and 350+ miles of Blue Ridge Parkway hiking trails to explore.  

It also features many important historic sites, such as the Cataloochee Valley and Mabry Mill. 

With less foliage on the trees and less traffic, Winter is a perfect time for spotting all types of birds and other wildlife.

Note that with the high elevations of the Blue Ridge Mountains and the unpredictable Winter weather in Virginia, it’s best to check the official BRP website for info on road closures before heading out on your adventure!

READ MORE: The 15 Best Blue Ridge Parkway Hotels & Cabin Rentals in NC & VA

Assateague Lighthouse in Assateague VA

3. Explore Assateague and Chincoteague Islands

Best known for the annual Chincoteague Pony Swim each July, the islands of Assateague and Chincoteague offer a unique Winter refuge for wildlife and visitors alike.

In Winter, Chincoteague is more of a sleepy fishing village than a booming beach town. With average temperatures of 50ºF, the area offers gorgeous ocean views, great restaurants, and plenty of shops.

The uninhabited barrier island of Assateague has the famous wild ponies, a windswept Atlantic beach, and a diverse population of birds, including Ospreys and Snow Geese.

While in Chincoteague, our lodging of choice is the Snug Harbor Marina & Resort, which offers amazing Winter sunsets and a perfect view of the Assateague Island Lighthouse across the bay.

READ MORE: 20 Beautiful Birds of Virginia

The Colonial Williamsburg Fifes & Drums

4. Grand Illumination at Colonial Williamsburg

The largest outdoor living history museum in America, Colonial Williamsburg is one of our favorite places to go in Virginia in Winter.

If you visit Virginia in December, you’ll find the authentic 18th century village alive with Christmas merriment, including Colonial-style Christmas decorations and appearances by Father Christmas.

With around 2,500 wreaths on the houses and outbuildings, it’s a festive pleasure to stroll the streets of Williamsburg. We also love Christmas shopping at Merchants Square, especially the Scottish-themed Scotland House.

Holiday festivities begin with a 5PM procession led by the Colonial Williamsburg Fifes & Drums, which is followed by a dazzling fireworks show at the Governor’s Mansion. It’s a great way to kick off the holiday season!

READ MORE: 10 Festive Things to Do in Shenandoah Valley VA for Christmas

Highland County Maple Festival in Virginia
Photo courtesy Highland County Chamber of Commerce

5. The Highland County Maple Festival

Known as “Virginia’s Little Switzerland,” Highland County has the highest average elevation in the state (2,832 feet). Its warm, sunny days and freezing nights also offer the perfect weather combo for maple sugar production!

The small town of Monterey is the county seat, and also the center of activity when the Highland Maple Festival starts. Since 1959, this beloved festival has been drawing visitors to learn about the syrup-making process.

You can choose one of 10 free sugar camp tours for a sweet educational experience. Then treat yourself to maple donuts, pancakes, or buckwheat cakes with real maple syrup.

The 2024 Highland County Maple Festival dates are March 9-10 and 16-17, and will include local food vendors and live entertainment (such as bluegrass music and clogging).

Note that visitors are advised to dress warmly and wear boots for the sugar camp tours. 

READ MORE: The 15 Best Virginia Music Festivals to Visit

Winter on Skyline Drive

6. Hiking on Skyline Drive

Shenandoah National Park‘s Skyline Drive is less than an hour from our home in Harrisonburg VA, and driving it is one of our favorite Winter activities in Virginia.

Due to high elevation, this National Scenic Byway gets more snow than the Shenandoah Valley. It stretches 105 miles on the crest of the Blue Ridge Mountains, with 75 scenic overlooks, cozy lodging, and some of the best hiking trails in VA.

One our favorite things to do in Virginia in Winter is to hike the Dark Hollow Falls Trail, which starts at milepost 50.7.

The closest of all the waterfalls off Skyline Drive, Dark Hollow Falls is a moderately difficult, 1.4-mile round-trip hike. The falls are 70 feet tall, and are transformed in winter with ice crystals and an incredible unobstructed view!

READ MORE: The 15 Best Virginia Waterfalls for Hiking

Golfing at Kingsmill Resort

7. Kingsmill Resort in Williamsburg

 Our favorite Winter getaway in Virginia is the Kingsmill Resort, a family-friendly resort in historic Williamsburg.

With mild Winter temps, I can play golf while Heather gets a massage at the resort’s luxury spa. With an indoor pool, hot tub, and world-class tennis facilities, there are amenities everyone in the family can enjoy.

Kingsmill is located on the James River, just minutes from historic Jamestown. We book a riverfront condo, so we can sit on the deck and spot birds of prey, deer, and the legendary “ghost fleet” on the river.

While there’s plenty to do at the resort, we always make time to visit Colonial Williamsburg and the greater Williamsburg area. The beautiful College of William & Mary is one of our favorite places to go for a brisk afternoon walk.

READ MORE:  The 10 Best Virginia Mountain Resorts to Visit

The Martha Washington Inn in Abingdon VA

8. Romantic Weekend at The Martha Washington

The Martha Washington Inn & Spa in Abingdon VA is one of our favorite romantic getaways in Virginia, with fluffy robes, a saltwater pool/hot tub, state-of-the-art spa, warm fires, and cozy common rooms.

Built in 1832 as a residence, it became a hotel in 1935, with 63 elegant rooms and suites filled with antique furniture.

We like to begin our day with a delicious free breakfast at their Sisters American Grill, then get a couples spa treatment.

Later we’ll hit the indoor saltwater swimming pool, or a soak in the outdoor saltwater hot tub, which is surrounded by beautiful foliage, fairy lights, and a waterfall.

After a date night, we’ll often end the day with a complimentary glass of port by the fireplace in the study.

READ MORE: 15 Great Romantic Getaways in Virginia for Couples

Massanutten Ski Resort in Massanutten VA

9. Snow Skiing at a Virginia Mountain Resort

Virginia has four awesome ski resorts to choose from, and one is close to our home in the Shenandoah Valley.

 Located 14 miles east of Harrisonburg VA, Massanutten is widely considered one of Virginia’s best ski resorts.

They offer Winter fun for the whole family, with skiing, snowboarding, ice skating, snow tubing, and even an indoor waterpark for off-the-slopes excitement.

With several great Massanutten Resort restaurants to choose from, you’ll also find plenty of après ski activities, as well as a full-service spa.

With the state of Virginia’s mild weather and Massanutten’s snow-making capabilities, the kids can have fun on the slopes while I golf with my buddies and Heather relaxes at the spa.

READ MORE:  The Best Ski Resorts in the Virginia Mountains to Visit

Photo courtesy Virginia Beach

10. Virginia Beach Boardwalk & Whale Watching

After the “boys of summer” are gone, Virginia Beach becomes a magical escape from the doldrums of Winter. With unencumbered views of the ocean, most of the boardwalk shops and restaurants are open, but not at all crowded.

Nature lovers will delight in the opportunity for whale-watching provided by the humpback whale migration in Virginia, which happens in January and February.

Book a guided tour with an experienced captain and crew to see Atlantic coast marine life, such as Dolphins, Seals, and Whales. You can sometimes spot whales in December, depending on water and air temperatures.

Marine lovers will also enjoy climate-controlled comfort at the Virginia Aquarium & Marine Science Center, which has over 800,000 gallons of marine exhibits and even hands-on-exhibits to explore.

For an outside-the-box Winter vacation in Virginia, we highly recommend Virginia Beach!  –by Heather Taylor & Jon Weaver; all photos by Jon Weaver & Heather Taylor unless otherwise noted; lead image courtesy Virginia Tourism 

Leave No Trace logo

We encourage anyone who loves the Blue Ridge region to learn about the Leave No Trace principles of responsible environmental stewardship. 

Stay on marked trails, take only pictures, pack out your trash, and be considerate of others who share the trails and parks you explore. 

Remember that waterfalls and rocky summits can be dangerous. Never try to climb waterfalls or get close to a ledge to get a selfie.

When you're exploring the wilderness, it's better to be safe than to be a statistic!

The universities brought Jon and Heather to Harrisonburg Virginia in the 1980s and the beauty of the Shenandoah Valley has kept them there to this day. Heather has a Master's Degree in Early Childhood Education and 10 years of experience as an editor and technical writer for online training sites. After college, Jon worked several years at a weekly newspaper before joining his family business which he ran until retirement. Jon and Heather enjoy traveling and sharing their stories with others. Locally, they love exploring the towns and mountains of the Blue Ridge near their hometown of Harrisonburg VA.