28 days in Virginia Itinerary
Created using Klarna Trips Virginia attractions planner
Start: Washington
Drive
1
Luray
— 3 nights
Drive
2
Shenandoah National Park
— 2 nights
Drive
3
Charlottesville
— 4 nights
Drive
4
Bedford
— 2 nights
Drive
5
Abingdon
— 2 nights
Fly
6
Williamsburg
— 4 nights
Drive
7
Virginia Beach
— 3 nights
Drive
8
Chincoteague Island
— 2 nights
Drive
9
Arlington
— 3 nights
Drive
10
Winchester
— 2 nights
Drive
End: Washington
Fri, Oct 21 - Thu, Nov 17
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Luray — 3 nights

Cabin Capital of Virginia
Venture out of the city with trips to Moving Meadows Farm (in Culpeper), Mt. Crawford Creamery (in Mount Crawford) and James Madison University (in Harrisonburg). There's lots more to do: Head underground at Luray Caverns, tour the pleasant surroundings at Stony Man Mountain Overlook, examine the collection at The Car and Carriage Caravan Museum, and get a dose of the wild on Raptor Hill Falconry.
For reviews, where to stay, traveler tips, and other tourist information, use the Luray visit website.
Washington to Luray is an approximately 1-hour car ride. In October, daytime highs in Luray are 70°F, while nighttime lows are 48°F. Finish your sightseeing early on the 24th (Mon) to allow enough time to drive to Shenandoah National Park.
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For reviews, where to stay, traveler tips, and other tourist information, use the Luray visit website.
Washington to Luray is an approximately 1-hour car ride. In October, daytime highs in Luray are 70°F, while nighttime lows are 48°F. Finish your sightseeing early on the 24th (Mon) to allow enough time to drive to Shenandoah National Park.
Side Trips
Sperryville, Showalter Orchard & Greenhouse, Whiteoak Canyon Falls, Shenandoah Valley Cultural Heritage Museum at The Edinburg Mill, Moving Meadows Farm
Find places to stay Oct 21 — 24:
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Shenandoah National Park — 2 nights

Kick off your visit on the 25th (Tue): trek along Limberlost Trail, then trek along Old Rag Mountain Hike, and then cruise along Skyline Drive. On the next day, explore the fascinating underground world of Grand Caverns, then take in the awesome beauty at Bearfence Mountain, and then take in the awesome beauty at Hawksbill Mountain.
To find traveler tips, ratings, maps, and tourist information, use the Shenandoah National Park visit planner.
Traveling by car from Luray to Shenandoah National Park takes 1.5 hours. In October, daily temperatures in Shenandoah National Park can reach 71°F, while at night they dip to 49°F. Finish your sightseeing early on the 26th (Wed) to allow enough time to drive to Charlottesville.
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To find traveler tips, ratings, maps, and tourist information, use the Shenandoah National Park visit planner.
Traveling by car from Luray to Shenandoah National Park takes 1.5 hours. In October, daily temperatures in Shenandoah National Park can reach 71°F, while at night they dip to 49°F. Finish your sightseeing early on the 26th (Wed) to allow enough time to drive to Charlottesville.
Side Trip
Find places to stay Oct 24 — 26:
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Charlottesville — 4 nights

Hoo-Ville
Change things up with these side-trips from Charlottesville: James Madison's Montpelier (in Montpelier Station), Central Virginia Wine Tours & Transportation (in Orange) and Somerset (Liberty Mills Farm & The Market at Grelen). There's still lots to do: admire the natural beauty at Monticello, experience rural life at Open Gate Farm, test your team's savvy at popular escape rooms, and get a taste of the local shopping with C'ville Arts: A Cooperative Gallery.
To see reviews, where to stay, more things to do, and more tourist information, you can read our Charlottesville journey planner.
You can drive from Shenandoah National Park to Charlottesville in 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 30th (Sun) early enough to drive to Bedford.
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To see reviews, where to stay, more things to do, and more tourist information, you can read our Charlottesville journey planner.
You can drive from Shenandoah National Park to Charlottesville in 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 30th (Sun) early enough to drive to Bedford.
Side Trips
Appomattox, Somerset, Open Gate Farm, James Madison's Montpelier, Central Virginia Wine Tours & Transportation
Find places to stay Oct 26 — 30:
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Bedford — 2 nights

Start off your visit on the 31st (Mon): experience rural life at A.J. Gross & Sons Orchard, then get engrossed in the history at Bedford Boys Tribute Center, and then appreciate the history behind National D-Day Memorial. On the 1st (Tue), you'll have a packed day of sightseeing: view the masterpieces at Earth, Fire, & Spirit Pottery, take in the dramatic natural features at Natural Bridge State Park, and then deepen your understanding at Virginia Military Institute.
To find more things to do, where to stay, other places to visit, and more tourist information, go to the Bedford online driving holiday planner.
Traveling by car from Charlottesville to Bedford takes 2 hours. In October, daily temperatures in Bedford can reach 70°F, while at night they dip to 47°F. Finish up your sightseeing early on the 1st (Tue) so you can go by car to Abingdon.
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To find more things to do, where to stay, other places to visit, and more tourist information, go to the Bedford online driving holiday planner.
Traveling by car from Charlottesville to Bedford takes 2 hours. In October, daily temperatures in Bedford can reach 70°F, while at night they dip to 47°F. Finish up your sightseeing early on the 1st (Tue) so you can go by car to Abingdon.
Side Trips
Find places to stay Oct 30 — Nov 1:
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Abingdon — 2 nights

Kick off your visit on the 2nd (Wed): admire the majestic nature at Grayson Highlands State Park, then hike along Virginia Creeper National Recreation Trail, and then explore the landscape on two wheels at Shuttle Shack. On your second day here, explore by horseback at Virginia Creeper Trail Club, then take a tour by water with South Holston River Company, then take an in-depth tour of The Birthplace of Country Music Museum, and finally view the masterpieces at Benjamin Walls Gallery.
To see ratings and tourist information, you can read our Abingdon trip itinerary planner.
Traveling by car from Bedford to Abingdon takes 3 hours. In November, plan for daily highs up to 57°F, and evening lows to 37°F. Wrap up your sightseeing on the 3rd (Thu) early enough to fly to Williamsburg.
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To see ratings and tourist information, you can read our Abingdon trip itinerary planner.
Traveling by car from Bedford to Abingdon takes 3 hours. In November, plan for daily highs up to 57°F, and evening lows to 37°F. Wrap up your sightseeing on the 3rd (Thu) early enough to fly to Williamsburg.
Side Trips
Find places to stay Nov 1 — 3:
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Williamsburg — 4 nights

Colonial Capital
Change things up with these side-trips from Williamsburg: Newport News (The Mariners' Museum and Park & The Noland Trail) and Windsor Castle Park (in Smithfield). Plan for a day of cool, family-friendly fun on the 5th (Sat) at Busch Gardens Williamsburg. The adventure continues: get engrossed in the history at Colonial Williamsburg, steep yourself in history at Jamestown Settlement, browse the exhibits of Historic Jamestowne, and look for gifts at Whitley's Peanut Factory.
To find maps, reviews, photos, and more tourist information, you can read our Williamsburg trip itinerary planning tool.
Getting from Abingdon to Williamsburg by flight takes about 5 hours. Other options: drive; or do a combination of taxi and bus. Traveling from Abingdon in November, expect nights in Williamsburg to be about the same, around 42°F, while days are a bit warmer, around 63°F. Finish up your sightseeing early on the 7th (Mon) so you can go by car to Virginia Beach.
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To find maps, reviews, photos, and more tourist information, you can read our Williamsburg trip itinerary planning tool.
Getting from Abingdon to Williamsburg by flight takes about 5 hours. Other options: drive; or do a combination of taxi and bus. Traveling from Abingdon in November, expect nights in Williamsburg to be about the same, around 42°F, while days are a bit warmer, around 63°F. Finish up your sightseeing early on the 7th (Mon) so you can go by car to Virginia Beach.
Side Trips
Find places to stay Nov 3 — 7:
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Virginia Beach — 3 nights

The Resort City
When in Virginia Beach, make a side trip to see Hickory Ridge Farm in Chesapeake, approximately Chesapeake away. There's still lots to do: take in the waterfront at Virginia Beach Boardwalk, enjoy the sand and surf at Virginia Beach, step aboard Battleship Wisconsin at Nauticus, and take a tour by water with Boat Tours & Water Sports.
For photos, reviews, traveler tips, and other tourist information, refer to the Virginia Beach visit website.
You can drive from Williamsburg to Virginia Beach in 1.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. In November, daytime highs in Virginia Beach are 62°F, while nighttime lows are 43°F. Finish up your sightseeing early on the 10th (Thu) so you can go by car to Chincoteague Island.
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For photos, reviews, traveler tips, and other tourist information, refer to the Virginia Beach visit website.
You can drive from Williamsburg to Virginia Beach in 1.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. In November, daytime highs in Virginia Beach are 62°F, while nighttime lows are 43°F. Finish up your sightseeing early on the 10th (Thu) so you can go by car to Chincoteague Island.
Side Trips
Find places to stay Nov 7 — 10:
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Chincoteague Island — 2 nights

On the 11th (Fri), look for all kinds of wild species at Chincoteague National Wildlife Refuge. On your second day here, explore the landscape on two wheels at Bike Depot, then see majestic marine mammals with a dolphin and whale watching tour, and then look for gifts at MamerSass.
To see other places to visit, maps, ratings, and other tourist information, read Chincoteague Island journey site.
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. Finish up your sightseeing early on the 12th (Sat) so you can go by car to Arlington.
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To see other places to visit, maps, ratings, and other tourist information, read Chincoteague Island journey site.
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. Finish up your sightseeing early on the 12th (Sat) so you can go by car to Arlington.
Find places to stay Nov 10 — 12:
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Arlington — 3 nights

National History, Local Flavor
Explore Arlington's surroundings by going to National Museum of the Marine Corps (in Triangle), George Washington's Mount Vernon (in Mount Vernon) 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 leisurely stroll along Old Town Waterfront, and get to know the fascinating history of The Tomb of the Unknown Soldier.
To see photos, traveler tips, and tourist information, refer to the Arlington tour itinerary planner.
Getting from Chincoteague Island to Arlington by car takes about 4 hours. Other options: 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. Wrap up your sightseeing on the 15th (Tue) early enough to drive to Winchester.
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To see photos, traveler tips, and tourist information, refer to the Arlington tour itinerary planner.
Getting from Chincoteague Island to Arlington by car takes about 4 hours. Other options: 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. Wrap up your sightseeing on the 15th (Tue) early enough to drive to Winchester.
Side Trips
Alexandria, National Museum of the Marine Corps, George Washington's Mount Vernon, Steven F. Udvar-Hazy Center, Room Escape Games
Find places to stay Nov 12 — 15:
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Winchester — 2 nights
Start off your visit on the 16th (Wed): take an in-depth tour of Stonewall Jackson's Headquarters, then get a taste of life in the country at Rocking S Ranch, then look for gifts at Marker-Miller Orchards, and finally learn about winemaking at Valerie Hill Vineyard & Winery. Get ready for a full day of sightseeing on the 17th (Thu): take in nature's colorful creations at State Arboretum of Virginia, then admire the majestic nature at Sky Meadows State Park, and then experience rural life at Hartland Family Orchard.
To find reviews, more things to do, maps, and other tourist information, read our Winchester route maker site.
Traveling by car from Arlington to Winchester takes 1.5 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of bus, train, and taxi. Traveling from Arlington in November, expect Winchester to be slightly colder, temps between 54°F and 35°F. Finish up your sightseeing early on the 17th (Thu) so you can go by car back home.
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To find reviews, more things to do, maps, and other tourist information, read our Winchester route maker site.
Traveling by car from Arlington to Winchester takes 1.5 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of bus, train, and taxi. Traveling from Arlington in November, expect Winchester to be slightly colder, temps between 54°F and 35°F. Finish up your sightseeing early on the 17th (Thu) so you can go by car back home.
Side Trips
Sky Meadows State Park, Valerie Hill Vineyard & Winery, Hartland Family Orchard, State Arboretum of Virginia
Find places to stay Nov 15 — 17:
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Virginia travel guide
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.