41 days in Virginia Itinerary

41 days in Virginia Itinerary

Created using Inspirock Virginia vacation planner
Make it your trip
Fly
1
Winchester
— 3 nights
Drive
2
Luray
— 5 nights
Drive
3
Arlington
— 5 nights
Drive
4
Chincoteague Island
— 4 nights
Drive
5
Virginia Beach
— 5 nights
Drive
6
Williamsburg
— 5 nights
Drive
7
Charlottesville
— 5 nights
Drive
8
Bedford
— 3 nights
Drive
9
Abingdon
— 5 nights
Drive to Asheville, Fly to Fresno

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Winchester — 3 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: Purcellville (The Washington & Old Dominion Trail & Catoctin Creek Distillery) and Sky Meadows State Park (in Delaplane). There's much more to do: wander the wide-open spaces of Rocking S Ranch, see the interesting displays at Stonewall Jackson's Headquarters, steep yourself in history at Belle Grove Plantation, and explore the world behind art at Museum of the Shenandoah Valley.

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

Fresno to Winchester is an approximately 8-hour flight. You can also drive; or do a combination of train, bus, and taxi. The time zone difference moving from Pacific Standard Time (PST) to Eastern Standard Time (EST) is 3 hours. Traveling from Fresno in September, expect Winchester to be a bit cooler, temps between 78°F and 56°F. Wrap up your sightseeing on the 23rd (Fri) early enough to drive to Luray.
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Museums · Parks · Nature · Trails
Side Trips
Find places to stay Sep 20 — 23:

Luray — 5 nights

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.
Explore the numerous day-trip ideas around Luray: SoLace Studios Fine Handcrafts (in Elkton), Shenandoah National Park (Hawksbill Mountain & Skyline Drive) and Mt. Crawford Creamery (in Mount Crawford). Next up on the itinerary: explore the stunning scenery at Luray Caverns, explore the fascinating underground world of Shenandoah Caverns, take an in-depth tour of The Car and Carriage Caravan Museum, and skim along the rocks with a canyoning and rapelling tour.

Plan my trip to Luray with suggested itineraries provided by Inspirock.

Traveling by car from Winchester to Luray takes 1.5 hours. In September in Luray, expect temperatures between 79°F during the day and 57°F at night. Wrap up your sightseeing on the 28th (Wed) early enough to drive to Arlington.
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Parks · Outdoors · Nature · Trails
Side Trips
Find places to stay Sep 23 — 28:

Arlington — 5 nights

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 National Museum of the Marine Corps (in Triangle). The adventure continues: stroll the grounds of Arlington National Cemetery, wander the streets of Old Town, make a trip to John F. Kennedy Grave Site, and see the interesting displays at Steven F. Udvar-Hazy Center.

To see photos, maps, traveler tips, and other tourist information, go to the Arlington trip planning app.

You can drive from Luray to Arlington in 2 hours. Alternatively, you can fly; or do a combination of taxi and bus. Traveling from Luray in September, plan for somewhat warmer nights in Arlington, with lows around 65°F. Finish your sightseeing early on the 3rd (Mon) so you can drive to Chincoteague Island.
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Historic Sites · Museums · Trails · Outdoors
Side Trips
Find places to stay Sep 28 — Oct 3:

Chincoteague Island — 4 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 4th (Tue) exploring nature at Chincoteague National Wildlife Refuge. There's still lots to do: see majestic marine mammals with a dolphin and whale watching tour, don't miss a visit to Chincoteague Cultural Alliance, go for a walk through Chincoteague Island Waterman's Memorial, and walk around Donald J. Leonard Park.

To find more things to do, where to stay, reviews, and tourist information, you can read our Chincoteague Island attractions planner.

Drive from Arlington to Chincoteague Island in 4 hours. Alternatively, you can do a combination of flight and bus; or do a combination of subway, train, bus, and taxi. Expect a daytime high around 71°F in October, and nighttime lows around 54°F. Finish up your sightseeing early on the 7th (Fri) so you can go by car to Virginia Beach.
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Parks · Wildlife · Nature · Outdoors
Side Trip
Find places to stay Oct 3 — 7:

Virginia Beach — 5 nights

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: Richmond (Capitol Square Park & Virginia Capitol Building). There's still lots to do: take a leisurely stroll along Virginia Beach Boardwalk, get a new perspective on things with Boat Tours & Water Sports, stroll through Virginia Beach, and take a tour of Battleship Wisconsin at Nauticus.

For traveler tips, reviews, where to stay, and more tourist information, refer to the Virginia Beach trip itinerary planning app.

Drive from Chincoteague Island to Virginia Beach in 2.5 hours. Alternatively, you can take a bus; or take a bus. In October in Virginia Beach, expect temperatures between 74°F during the day and 56°F at night. Cap off your sightseeing on the 12th (Wed) early enough to go by car to Williamsburg.
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Parks · Museums · Outdoors · Beaches
Side Trips
Find places to stay Oct 7 — 12:

Williamsburg — 5 nights

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.
Get out of town with these interesting Williamsburg side-trips: St. Luke's Historic Church & Museum (in Smithfield) and The Mariners' Museum & Park (in Newport News). Spend the 16th (Sun) exploring nature at Colonial National Historical Park. There's much more to do: steep yourself in history at Colonial Williamsburg, explore the galleries of Historic Jamestowne, cool off at Busch Gardens Williamsburg, and take a tour of Jamestown Settlement.

To see more things to do, ratings, maps, and tourist information, read Williamsburg trip planner.

Drive from Virginia Beach to Williamsburg in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In October, plan for daily highs up to 75°F, and evening lows to 55°F. Finish your sightseeing early on the 17th (Mon) to allow enough time to drive to Charlottesville.
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Historic Sites · Museums · Parks · Nature
Side Trips
Find places to stay Oct 12 — 17:

Charlottesville — 5 nights

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 Charlottesville's surroundings by going to Old Rag Mountain Hike (in Shenandoah National Park), Appomattox Court House National Historical Park (in Appomattox) and Natural Bridge (Virginia Safari Park & Natural Bridge State Park). And it doesn't end there: take in nature's colorful creations at Monticello, experience rural life at Open Gate Farm, indulge your senses at Central Virginia Wine Tours & Transportation, and steep yourself in history at Mulberry Row.

To find other places to visit, ratings, photos, and tourist information, read Charlottesville trip itinerary tool.

Traveling by car from Williamsburg to Charlottesville takes 2.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. Traveling from Williamsburg in October, Charlottesville is slightly colder at night with lows of 49°F. Finish your sightseeing early on the 22nd (Sat) to allow enough time to drive to Bedford.
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Historic Sites · Parks · Nature · Tours
Side Trips
Find places to stay Oct 17 — 22:

Bedford — 3 nights

Bedford is an incorporated town and former independent city located within Bedford County in the U.S. state of Virginia. Explore the numerous day-trip ideas around Bedford: Patrick Henry's Red Hill (in Brookneal), Smith Mountain Lake (in Moneta) and Booker T. Washington National Monument (in Hardy). There's still lots to do: appreciate the history behind National D-Day Memorial, relax in the rural setting at A.J. Gross & Sons Orchard, and admire the landmark architecture of Thomas Jefferson's Poplar Forest.

To find other places to visit, traveler tips, ratings, and more tourist information, use the Bedford driving holiday planning tool.

Drive from Charlottesville to Bedford in 2 hours. Alternatively, you can drive. October in Bedford sees daily highs of 70°F and lows of 47°F at night. Finish your sightseeing early on the 25th (Tue) to allow enough time to drive to Abingdon.
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Historic Sites · Nature · Parks · Museums
Side Trips
Find places to stay Oct 22 — 25:

Abingdon — 5 nights

Abingdon is a town in Washington County, Virginia, United States, southwest of Roanoke. Go for a jaunt from Abingdon to Mouth of Wilson to see Grayson Highlands State Park about 48 minutes away. There's lots more to do: trek along Virginia Creeper National Recreation Trail, grab your bike and head to Shuttle Shack, see the interesting displays at Star Museum, and gear up at Adventure Damascus.

To find photos, reviews, and other tourist information, go to the Abingdon trip itinerary maker.

Drive from Bedford to Abingdon in 3 hours. Alternatively, you can drive. In October, daytime highs in Abingdon are 69°F, while nighttime lows are 49°F. Wrap up your sightseeing on the 30th (Sun) early enough to travel back home.
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Parks · Trails · Outdoors · Museums
Side Trips
Find places to stay Oct 25 — 30:

Virginia travel guide

4.6
Historic Sites · Wineries & Vineyards · Gardens
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.
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