56 days in Virginia Itinerary

56 days in Virginia Itinerary

Created using Inspirock Virginia trip maker

Make it your trip
Drive
1
Luray
— 5 nights
Drive
2
Shenandoah National Park
— 6 nights
Drive
3
Charlottesville
— 6 nights
Drive
4
Lexington
— 6 nights
Drive
5
Abingdon
— 5 nights
Fly
6
Williamsburg
— 6 nights
Drive
7
Virginia Beach
— 5 nights
Drive
8
Chincoteague Island
— 5 nights
Drive
9
Arlington
— 6 nights
Drive
10
Winchester
— 5 nights
Drive

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Luray

— 5 nights

Cabin Capital of Virginia

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.
Change things up with these side-trips from Luray: Moving Meadows Farm (in Culpeper), R.H. Ballard Shop & Gallery (in Washington) and Buzzard Rock North (in Front Royal). There's much more to do: explore the fascinating underground world of Luray Caverns, hike along Kennedy Peak Hike, stroll through Whiteoak Canyon Falls, and relax in the rural setting at Showalter Orchard & Greenhouse.

For reviews, other places to visit, and more tourist information, use the Luray trip planner.

Washington to Luray is an approximately 1-hour car ride. October in Luray sees daily highs of 70°F and lows of 48°F at night. Finish your sightseeing early on the 11th (Mon) so you can drive to Shenandoah National Park.

Things to do in Luray

Parks · Outdoors · Trails · Museums

Side Trips

Find places to stay Oct 6 — 11:

Shenandoah National Park

— 6 nights
Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.
You'll find plenty of places to visit near Shenandoah National Park: SoLace Studios Fine Handcrafts (in Elkton), Grand Caverns (in Grottoes) and Augusta Military Academy Museum (in Fort Defiance). The adventure continues: admire all the interesting features of Skyline Drive, trek along Limberlost Trail, stroll through Mary's Rock Summit Trail, and take in the awesome beauty at Hawksbill Mountain.

To see photos, where to stay, ratings, and tourist information, go to the Shenandoah National Park trip maker.

Traveling by car from Luray to Shenandoah National Park takes 1.5 hours. Expect a daytime high around 71°F in October, and nighttime lows around 49°F. Finish your sightseeing early on the 17th (Sun) so you can drive to Charlottesville.

Things to do in Shenandoah National Park

Parks · Outdoors · Trails · Nature

Side Trips

Find places to stay Oct 11 — 17:

Charlottesville

— 6 nights

Hoo-Ville

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.
You'll find plenty of places to visit near Charlottesville: Chateau MerrillAnne LLC (in Orange), Appomattox Court House National Historical Park (in Appomattox) and James Madison's Montpelier (in Montpelier Station). And it doesn't end there: steep yourself in history at Monticello, indulge your senses at some of the top wineries in the area, get engrossed in the history at Frontier Culture Museum, and relax in the rural setting at Open Gate Farm.

To see other places to visit, maps, photos, and tourist information, go to the Charlottesville trip maker site.

Getting from Shenandoah National Park to Charlottesville by car takes about 1.5 hours. In October, daily temperatures in Charlottesville can reach 71°F, while at night they dip to 49°F. Wrap up your sightseeing on the 23rd (Sat) early enough to drive to Lexington.

Things to do in Charlottesville

Historic Sites · Parks · Nature · Museums

Side Trips

Find places to stay Oct 17 — 23:

Lexington

— 6 nights
Home to two prestigious educational institutions, Lexington was founded in 1778.
Change things up with these side-trips from Lexington: The American Civil War Museum - Appomattox (in Appomattox), Blackwater Creek Trail (in Lynchburg) and Seamans’ Orchard (in Roseland). And it doesn't end there: pause for some photo ops at National D-Day Memorial, steep yourself in history at Stonewall Jackson House, get engrossed in the history at Lee Chapel and Museum, and stroll through Natural Bridge State Park.

To plan Lexington vacation without wasting time, ask Inspirock to design an itinerary.

Getting from Charlottesville to Lexington by car takes about 1.5 hours. Other options: do a combination of train and taxi. Traveling from Charlottesville in October, you will find days in Lexington are little chillier (59°F), and nights are about the same (45°F). Finish your sightseeing early on the 29th (Fri) so you can drive to Abingdon.

Things to do in Lexington

Parks · Nature · Museums · Historic Sites

Side Trips

Find places to stay Oct 23 — 29:

Abingdon

— 5 nights
Abingdon is a town in Washington County, Virginia, United States, southwest of Roanoke. Step out of Abingdon to go to Mouth of Wilson and see Grayson Highlands State Park, which is approximately 1h 5 min away. There's lots more to do: trek along Virginia Creeper National Recreation Trail, take an in-depth tour of The Birthplace of Country Music Museum, gear up at Shuttle Shack, and see the interesting displays at Fields-Penn 1860 House Museum.

To find photos, maps, and other tourist information, read our Abingdon trip itinerary builder site.

Drive from Lexington to Abingdon in 3 hours. Alternatively, you can fly; or do a combination of bus and taxi. When traveling from Lexington in October, plan for somewhat warmer days in Abingdon, with highs around 69°F, while nights are about the same with lows around 49°F. Cap off your sightseeing on the 3rd (Wed) early enough to catch the flight to Williamsburg.

Things to do in Abingdon

Parks · Trails · Outdoors · Museums

Side Trips

Find places to stay Oct 29 — Nov 3:

Williamsburg

— 6 nights

Colonial Capital

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.
You'll find plenty of places to visit near Williamsburg: Smithfield (Windsor Castle Park & St. Luke's Historic Church & Museum) and Newport News (The Mariners' Museum & Park & The Noland Trail). There's lots more to do: get engrossed in the history at Colonial Williamsburg, explore the galleries of Historic Jamestowne, take in the history at American Revolution Museum at Yorktown, and find something for the whole family at Busch Gardens Williamsburg.

To see more things to do, where to stay, ratings, and tourist information, read Williamsburg day trip planning tool.

You can fly from Abingdon to Williamsburg in 5 hours. Other options are to drive; or do a combination of taxi and bus. When traveling from Abingdon in November, plan for somewhat warmer days in Williamsburg, with highs around 63°F, while nights are about the same with lows around 42°F. Finish your sightseeing early on the 9th (Tue) so you can drive to Virginia Beach.

Things to do in Williamsburg

Historic Sites · Museums · Parks · Shopping

Side Trips

Find places to stay Nov 3 — 9:

Virginia Beach

— 5 nights

The Resort City

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.
Explore Virginia Beach's surroundings by going to Spas (in Chesapeake), Blandford Church and Cemetery (in Petersburg) and Suffolk Seaboard Station Railroad Museum (in Suffolk). Next up on the itinerary: take in the waterfront at Virginia Beach Boardwalk, take a pleasant ride with a tour on horseback, get up close and personal with brilliant marine life at Virginia Aquarium & Marine Science Center, and experience rural life at New Earth Farm.

For photos, traveler tips, maps, and other tourist information, read Virginia Beach trip planner.

You can drive from Williamsburg to Virginia Beach in 1.5 hours. Other options are to take a bus; or do a combination of train and bus. Expect a daytime high around 62°F in November, and nighttime lows around 43°F. Wrap up your sightseeing on the 14th (Sun) early enough to drive to Chincoteague Island.

Things to do in Virginia Beach

Museums · Outdoors · Parks · Historic Sites

Side Trips

Find places to stay Nov 9 — 14:

Chincoteague Island

— 5 nights
Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Spend the 15th (Mon) exploring nature at Chincoteague National Wildlife Refuge. And it doesn't end there: get outside with Captain Dan's Around the Island Tours, go for a walk through Chincoteague Island Waterman's Memorial, don't miss a visit to Chincoteague Cultural Alliance, and examine the collection at Chincoteague Bay Field Station.

To see traveler tips, ratings, reviews, and other tourist information, refer to the Chincoteague Island planner.

Traveling by car from Virginia Beach to Chincoteague Island takes 2.5 hours. Alternatively, you can take a bus; or take a bus. November in Chincoteague Island sees daily highs of 59°F and lows of 40°F at night. Cap off your sightseeing on the 19th (Fri) early enough to go by car to Arlington.

Things to do in Chincoteague Island

Parks · Wildlife · Nature · Outdoors

Side Trip

Find places to stay Nov 14 — 19:

Arlington

— 6 nights

National History, Local Flavor

Located just across the Potomac River from Washington, D.C., the county of Arlington blends big city and sprawling suburban environments.
Explore the numerous day-trip ideas around Arlington: George Washington's Mount Vernon (in Mount Vernon), Manassas National Battlefield Park (in Manassas) and Steven F. Udvar-Hazy Center (in Chantilly). There's much more to do: stroll the grounds of Arlington National Cemetery, pause for some photo ops at U.S. Marine Corps War Memorial, take a stroll through Old Town, and bet on your favorite at Dominion Speedway.

To find ratings, photos, more things to do, and other tourist information, read Arlington route planning app.

You can drive from Chincoteague Island to Arlington in 4 hours. Other options are to do a combination of bus and flight; or do a combination of taxi, bus, train, and subway. Expect a daytime high around 59°F in November, and nighttime lows around 42°F. Finish your sightseeing early on the 25th (Thu) so you can drive to Winchester.

Things to do in Arlington

Historic Sites · Parks · Museums · Trails

Side Trips

Find places to stay Nov 19 — 25:

Winchester

— 5 nights
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Get out of town with these interesting Winchester side-trips: Raven Rocks (in Bluemont), Markham (Hartland Family Orchard & Stribling Orchard) and The Washington & Old Dominion Trail (in Purcellville). There's still lots to do: get a taste of life in the country at Rocking S Ranch, take an in-depth tour of Stonewall Jackson's Headquarters, admire the majestic nature at Sky Meadows State Park, and stop by Marker-Miller Orchards.

Planning Winchester trip won't be overwhelming when you use Inspirock's itinerary maker.

You can drive from Arlington to Winchester in 1.5 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of subway, train, and taxi. Traveling from Arlington in November, expect Winchester to be little chillier, temps between 54°F and 35°F. Finish up your sightseeing early on the 30th (Tue) so you can go by car back home.

Things to do in Winchester

Outdoors · Parks · Trails · Museums

Side Trips

Find places to stay Nov 25 — 30:

Virginia travel guide

4.6
History Museums · Wineries & Vineyards · Historic Sites
Old Dominion
The home of the first permanent English colony in the New World, Virginia is a prime holiday destination for those looking to immerse themselves in American heritage. Proud of its colorful history, distinct culture, and southern drawl, Virginians see their state as the place where the imaginary line between the north and the south is drawn. With scenic beauties as diverse as its people, Virginia is a land of rolling hills, rugged mountains, lush valleys, dense forests, and secluded beaches along picturesque bays. Bordered on the east by the Atlantic and the west by the Appalachian Mountains, with rolling farmland in the middle, the state offers countless places to visit for history buffs, nature lovers, and passionate foodies.