50 days in Virginia Itinerary

50 days in Virginia Itinerary

Created using Inspirock Virginia trip planner

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Route & dates

50 days in Virginia Itinerary

Start: Roanoke
Drive:  45​min
1
Bedford
— 3 nights
Drive:  1​h 45​min
2
Charlottesville
— 6 nights
Drive:  2​h 15​min
3
Williamsburg
— 6 nights
Drive:  1​h 15​min
4
Virginia Beach
— 6 nights
Drive:  2​h 30​min
5
Chincoteague Island
— 5 nights
Drive:  3​h 45​min
6
Arlington
— 5 nights
Drive:  1​h 30​min
7
Winchester
— 5 nights
Drive:  1​h 15​min
8
Luray
— 5 nights
Drive:  1​h 15​min
9
Shenandoah National Park
— 5 nights
Drive:  4​h 15​min
10
Damascus
— 3 nights
Drive:  2​h 15​min
End: Roanoke

3
nights
Bedford

Bedford ©
Bedford is an incorporated town and former independent city located within Bedford County in the U.S. Change things up with these side-trips from Bedford: Natural Bridge (Natural Bridge State Park, Dinosaur Kingdom II, & more), Lexington (Earth, Fire, & Spirit Pottery, Virginia Military Institute, & more) and Roanoke (Carvins Cove Natural Reserve, St. John's Episcopal Church, & more). There's much more to do: appreciate the history behind National D-Day Memorial, admire the natural beauty at Hahn Horticulture Garden at Virginia Tech, and get a taste of the local shopping with The Little Gallery.

To see where to stay, other places to visit, photos, and other tourist information, read Bedford trip itinerary tool .

Roanoke to Bedford is an approximately 1-hour car ride. Expect a daytime high around 58°F in November, and nighttime lows around 35°F. Wrap up your sightseeing on the 8th (Fri) to allow time to travel to Charlottesville.

Things to do in Bedford

Parks Wildlife Museums

Side Trips

Roanoke, Lexington, Natural Bridge, Hahn Horticulture Garden at Virginia Tech
Highlights from your plan
National D-Day Memorial ©
National D-Day Memorial
Virginia Military Institute ©
Virginia Military Institute
Natural Bridge State Park ©
Natural Bridge State Park

6
nights
Charlottesville

Charlottesville ©
Situated at the foothills of the Blue Ridge Mountains, Charlottesville is perhaps best known as the home of three of the United States' founding fathers, including Thomas Jefferson.
Explore the numerous day-trip ideas around Charlottesville: James Madison's Montpelier (in Montpelier Station), Canal Basin Square (in Scottsville) and The Quarry Gardens (in Schuyler). The adventure continues: take in nature's colorful creations at Monticello, test your problem-solving skills at popular escape rooms, learn the secrets of beer at a beer tour and tasting, and head outdoors with Cavalier Sporting Clays.

To see traveler tips, maps, and more tourist information, use the Charlottesville online route maker .

Drive from Bedford to Charlottesville in 2 hours. In November, plan for daily highs up to 59°F, and evening lows to 37°F. Cap off your sightseeing on the 14th (Thu) early enough to go by car to Williamsburg.

Things to do in Charlottesville

Parks Outdoors Trails

Side Trips

Staunton, Open Gate Farm, James Madison's Montpelier, Cavalier Sporting Clays, The Quarry Gardens
Highlights from your plan
Monticello ©
Monticello
Carter Mountain Orchard ©
Carter Mountain Orchard
Beer Tastings & Tours

6
nights
Williamsburg

Williamsburg ©
Founded in 1632 as a fortified settlement on the high ground between two rivers, Williamsburg served as a colonial capital of Virginia for over 80 years.
Venture out of the city with trips to Richmond (Virginia Museum of Fine Arts & Maymont), Newport News (The Noland Trail & The Mariners' Museum & Park) and Smithfield (St. Luke's Historic Church & Museum & Windsor Castle Park). There's much more to do: contemplate the long history of Colonial Williamsburg, take an in-depth tour of Historic Jamestowne, explore the wealth of natural beauty at Colonial National Historical Park, and stop by Quirks of Art.

For maps, other places to visit, and other tourist information, read our Williamsburg trip itinerary planner .

Drive from Charlottesville to Williamsburg in 2.5 hours. Alternatively, you can take a bus. In November, plan for daily highs up to 63°F, and evening lows to 42°F. Finish up your sightseeing early on the 20th (Wed) so you can go by car to Virginia Beach.

Things to do in Williamsburg

Historic Sites Museums Parks

Side Trips

Smithfield, Richmond, Newport News, Nelson House
Highlights from your plan
Colonial Williamsburg ©
Colonial Williamsburg
Busch Gardens Williamsburg ©
Busch Gardens Williamsburg
Historic Jamestowne ©
Historic Jamestowne

6
nights
Virginia Beach

Virginia Beach ©
Holding a record for the longest pleasure beach in the world, Virginia Beach showcases 35 miles of coastline and maintains a longstanding reputation as a family-friendly vacation destination.
Get out of town with these interesting Virginia Beach side-trips: Weyanoke Bird and Wildflower Sanctuary (in Norfolk), Bay Creek Golf Club (in Cape Charles) and Planters Peanut Center (in Suffolk). There's much more to do: take in the waterfront at Virginia Beach Boardwalk, step aboard Battleship Wisconsin, get outside with Matador Sport Fishing Charters, and learn about all things military at Military Aviation Museum.

Use Inspirock's suggestions to plan your Virginia Beach trip and find the best activities and attractions for your vacation.

Getting from Williamsburg to Virginia Beach by car takes about 1.5 hours. Other options: take a bus; or take a bus. In November in Virginia Beach, expect temperatures between 62°F during the day and 43°F at night. Wrap up your sightseeing on the 26th (Tue) to allow time to drive to Chincoteague Island.

Things to do in Virginia Beach

Parks Museums Outdoors

Side Trips

Norfolk, Planters Peanut Center, Bay Creek Golf Club
Highlights from your plan
Tarnished Truth Distilling Company ©
Virginia Beach Boardwalk ©
Virginia Beach Boardwalk
Military Aviation Museum ©
Military Aviation Museum

5
nights
Chincoteague Island

Chincoteague Island ©
Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Venture out of the city with trips to Onancock (Hopkins & Bros. Store & Ker Place). There's still lots to do: explore the striking landscape of Chincoteague National Wildlife Refuge, take in the pleasant sights at Chincoteague Island Waterman's Memorial, head outdoors with Donald J. Leonard, and grab your bike and head to Bike Depot.

To find ratings, traveler tips, other places to visit, and other tourist information, use the Chincoteague Island road trip tool .

You can drive from Virginia Beach to Chincoteague Island in 2.5 hours. Other options are to take a bus; or take a bus. In November in Chincoteague Island, expect temperatures between 59°F during the day and 40°F at night. Finish up your sightseeing early on the 1st (Sun) so you can go by car to Arlington.

Things to do in Chincoteague Island

Parks Museums Wildlife

Side Trips

Onancock, Chincoteague Bay Field Station
Highlights from your plan
Chincoteague National Wildlife Refuge ©
Nature & Wildlife Tours
Chincoteague Veteran's Memorial Park ©

5
nights
Arlington

Arlington ©
Located just across the Potomac River from Washington, D.C., the county of Arlington blends big city and sprawling suburban environments.
Explore Arlington's surroundings by going to National Museum of the Marine Corps (in Triangle), Steven F. Udvar-Hazy Center (in Chantilly) and Aslin Brewery (in Herndon). And it doesn't end there: stroll the grounds of Arlington National Cemetery, explore the landscape on two wheels at Mount Vernon Trail, step off the mainland to explore Theodore Roosevelt Island Park, and appreciate the history behind U.S. Marine Corps War Memorial.

For ratings, photos, where to stay, and other tourist information, read Arlington trip planner .

Traveling by car from Chincoteague Island to Arlington takes 4 hours. Alternatively, you can do a combination of bus and flight; or do a combination of taxi and bus. In December, plan for daily highs up to 51°F, and evening lows to 37°F. Cap off your sightseeing on the 6th (Fri) early enough to go by car to Winchester.

Things to do in Arlington

Parks Historic Sites Museums

Side Trips

Old Town, George Washington's Mount Vernon, Steven F. Udvar-Hazy Center, Audubon Naturalist Society Rust Nature Sanctuary, National Museum of the Marine Corps
Highlights from your plan
The Tomb of the Unknown Soldier ©
The Tomb of the Unknown Soldier
Arlington National Cemetery ©
Arlington National Cemetery
Steven F. Udvar-Hazy Center ©
Steven F. Udvar-Hazy Center

5
nights
Winchester

Winchester ©
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. You'll find plenty of places to visit near Winchester: Purcellville (Blue Ridge Center for Environmental Stewardship & The Washington & Old Dominion Trail), Raven Rocks (in Bluemont) and Royal Horseshoe Farm (in Front Royal). There's much more to do: get a taste of life in the country at Rocking S Ranch, walk around Sherando Park, get engrossed in the history at Virginia Museum of Veiled History, and admire the majestic nature at Sky Meadows State Park.

For maps, where to stay, ratings, and other tourist information, read our Winchester online trip itinerary planner .

Traveling by car from Arlington to Winchester takes 1.5 hours. Alternatively, you can take a bus; or take a train. Traveling from Arlington in December, Winchester is little chillier at night with lows of 31°F. Finish up your sightseeing early on the 11th (Wed) so you can go by car to Luray.

Things to do in Winchester

Parks Nature Outdoors

Side Trips

Purcellville, My Neighbor and Me, Cedar Creek & Belle Grove National Historical Park Visitors Contact Station, Raven Rocks, Sherando Park
Highlights from your plan
Rocking S Ranch ©
Rocking S Ranch
Cascade Falls ©
Cascade Falls
Raven Rocks ©
Raven Rocks

5
nights
Luray

Luray ©
Nestled in the heart of the valley formed by the Shenandoah River, Luray draws visitors with a vast underground cavern system adorned with stalactites, stalagmites, and mirrored pools.
Venture out of the city with trips to Front Royal (Buzzard Rock North & Balthis House), Big Schloss (in Woodstock) and Harrisonburg (Explore More Discovery Museum & Harper's Statuary and Water Gardens). And it doesn't end there: take in breathtaking views at Luray Caverns, trek along Kennedy Peak Hike, see the interesting displays at The Car and Carriage Caravan Museum, and tour the pleasant surroundings at Little Devil's Stairs Trail.

To see reviews, other places to visit, traveler tips, and more tourist information, use the Luray route planner.

You can drive from Winchester to Luray in 1.5 hours. In December, plan for daily highs up to 50°F, and evening lows to 32°F. Wrap up your sightseeing on the 16th (Mon) to allow time to drive to Shenandoah National Park.

Things to do in Luray

Parks Outdoors Trails

Side Trips

Sperryville, Front Royal, Harrisonburg, Big Schloss, White Oak Canyon Trail
Highlights from your plan
Luray Caverns ©
Luray Caverns
Stony Man Mountain Overlook ©
Stony Man Mountain Overlook
Birdsong Pleasure Garden ©
Birdsong Pleasure Garden

5
nights
Shenandoah National Park

Shenandoah National Park ©
Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.
Venture out of the city with trips to SoLace Studios Fine Handcrafts (in Elkton), Brix and Columns Vineyards (in McGaheysville) and Harrisonburg (A Dream Come True Playground, Mineral Museum, & more). The adventure continues: contemplate the waterfront views at Skyline Drive, explore the different monuments and memorials at Dean Cemetery, trek along Old Rag Mountain Hike, and take in the awesome beauty at Pinnacles.

To see reviews, photos, more things to do, and more tourist information, you can read our Shenandoah National Park holiday site .

Drive from Luray to Shenandoah National Park in 1.5 hours. In December, plan for daily highs up to 52°F, and evening lows to 34°F. Finish up your sightseeing early on the 21st (Sat) so you can travel to Damascus.

Things to do in Shenandoah National Park

Outdoors Parks Nature

Side Trips

Harrisonburg, Port Republic Museum, Brix and Columns Vineyards, SoLace Studios Fine Handcrafts, Highland County Museum
Highlights from your plan
Old Rag Mountain Hike ©
Old Rag Mountain Hike
Skyline Drive ©
Skyline Drive
Mary's Rock Summit Trail ©
Mary's Rock Summit Trail

3
nights
Damascus

Damascus ©
Damascus is a town in Washington County, Virginia, United States. Venture out of the city with trips to Grayson Highlands State Park (in Mouth of Wilson), Beaver Dam Creek Walking Trail (in Hillsville) and The Blue Ridge Music Center (in Galax). There's lots more to do: trek along Virginia Creeper National Recreation Trail, stroll through The Channels Natural Area Preserve, see the interesting displays at Fields-Penn 1860 House Museum, and steep yourself in history at Haller-Gibboney Rock House.

To find traveler tips, where to stay, and more tourist information, you can read our Damascus tour itinerary maker site .

Traveling by car from Shenandoah National Park to Damascus takes 4.5 hours. Alternatively, you can do a combination of car and flight. Expect a daytime high around 51°F in December, and nighttime lows around 35°F. Cap off your sightseeing on the 24th (Tue) early enough to travel back home.

Things to do in Damascus

Parks Trails Outdoors

Side Trips

Fields-Penn 1860 House Museum, Haller-Gibboney Rock House, The Channels Natural Area Preserve, Grayson Highlands State Park, The Blue Ridge Music Center
Highlights from your plan
Grayson Highlands State Park ©
Grayson Highlands State Park
The Blue Ridge Music Center ©
The Blue Ridge Music Center

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