32 days in Virginia Itinerary

32 days in Virginia Itinerary

Created using Inspirock Virginia tour itinerary builder

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Route & dates

32 days in Virginia Itinerary

Start: Newark
Fly:  3​h
1
Arlington
— 3 nights
Drive:  1​h 30​min
2
Winchester
— 3 nights
Drive:  1​h 15​min
3
Luray
— 3 nights
Drive:  1​h 15​min
4
Shenandoah National Park
— 4 nights
Drive:  4​h 30​min
5
Damascus
— 1 night
Drive:  3​h 45​min
6
Charlottesville
— 4 nights
bus:  1​h 15​min
7
Richmond
— 4 nights
Drive:  3​h 45​min
8
Chincoteague Island
— 4 nights
Drive:  2​h 30​min
9
Virginia Beach
— 5 nights
Fly:  3​h 15​min
End: Newark

3
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 Steven F. Udvar-Hazy Center (in Chantilly), Quantico National Cemetery (in Quantico) and National Museum of the Marine Corps (in Triangle). There's lots more to do: stroll the grounds of Arlington National Cemetery, examine the collection at George Washington's Mount Vernon, explore the landscape on two wheels at Mount Vernon Trail, and get to know the fascinating history of The Tomb of the Unknown Soldier.

Plan a Arlington trip in moments using our itinerary builder.

Newark to Arlington is an approximately 3-hour flight. You can also do a combination of flight, bus, and subway; or drive. In October in Arlington, expect temperatures between 71°F during the day and 54°F at night. Finish up your sightseeing early on the 21st (Mon) so you can go by car to Winchester.

Things to do in Arlington

Historic Sites Museums Parks

Side Trips

Alexandria, George Washington's Mount Vernon, National Museum of the Marine Corps, Steven F. Udvar-Hazy Center, Quantico National Cemetery
Find places to stay Oct 18 — 21:
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

3
nights
Winchester

Winchester ©
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Change things up with these side-trips from Winchester: Raven Rocks (in Bluemont), Sky Meadows State Park (in Delaplane) and Purcellville (The Washington & Old Dominion Trail & Blue Ridge Center for Environmental Stewardship). There's still lots to do: wander the wide-open spaces of Rocking S Ranch, admire the sheer force of Cascade Falls, get lost in a book at Handley Regional Library, and take an in-depth tour of Museum of the Shenandoah Valley.

For photos, other places to visit, reviews, and other tourist information, go to the Winchester trip itinerary planner.

Traveling by car from Arlington to Winchester takes 1.5 hours. Alternatively, you can take a bus; or take a train. Plan for a bit cooler nights when traveling from Arlington in October since evenings lows in Winchester dip to 46°F. Cap off your sightseeing on the 24th (Thu) early enough to go by car to Luray.

Things to do in Winchester

Parks Outdoors Trails

Side Trips

Purcellville, Cascade Falls, Raven Rocks, Sky Meadows State Park
Find places to stay Oct 21 — 24:
Highlights from your plan
Rocking S Ranch ©
Rocking S Ranch
Cascade Falls ©
Cascade Falls
Museum of the Shenandoah Valley ©
Museum of the Shenandoah Valley

3
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.
Explore Luray's surroundings by going to Buzzard Rock North (in Front Royal) and Moving Meadows Farm (in Culpeper). And it doesn't end there: explore the stunning scenery at Luray Caverns, take an in-depth tour of The Car and Carriage Caravan Museum, Head underground at Shenandoah Caverns, and trek along Kennedy Peak Hike.

To find where to stay, traveler tips, other places to visit, and more tourist information, read Luray trip itinerary planning tool .

Drive from Winchester to Luray in 1.5 hours. In October, daily temperatures in Luray can reach 70°F, while at night they dip to 48°F. Wrap up your sightseeing on the 27th (Sun) early enough to drive to Shenandoah National Park.

Things to do in Luray

Parks Outdoors Trails

Side Trips

Shenandoah Caverns, Buzzard Rock North, Moving Meadows Farm, Meems Bottom Covered Bridge, Copper Fox Distillery
Find places to stay Oct 24 — 27:
Highlights from your plan
Luray Caverns ©
Luray Caverns
Stony Man Mountain Overlook ©
Stony Man Mountain Overlook
Birdsong Pleasure Garden ©
Birdsong Pleasure Garden

4
nights
Shenandoah National Park

Shenandoah National Park ©
Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.
Explore the numerous day-trip ideas around Shenandoah National Park: SoLace Studios Fine Handcrafts (in Elkton), Mt. Crawford Creamery (in Mount Crawford) and Grand Caverns (in Grottoes). There's much more to do: take a memorable drive along Skyline Drive, explore the different monuments and memorials at Dean Cemetery, take in the awesome beauty at Bearfence Mountain, and hike along Mary's Rock Summit Trail.

Plan my day in Shenandoah National Park using traveler tips and tourist information provided by Inspirock.

Drive from Luray to Shenandoah National Park in 1.5 hours. Expect a daytime high around 71°F in October, and nighttime lows around 49°F. Finish up your sightseeing early on the 31st (Thu) so you can travel to Damascus.

Things to do in Shenandoah National Park

Parks Outdoors Nature

Side Trips

Grand Caverns, SoLace Studios Fine Handcrafts, Mt. Crawford Creamery, White Oak Lavender Farm & The Purple WOLF Vineyard
Find places to stay Oct 27 — 31:
Highlights from your plan
Old Rag Mountain Hike ©
Old Rag Mountain Hike
Skyline Drive ©
Skyline Drive
Appalachian Trail ©
Appalachian Trail

1
night
Damascus

Damascus ©
Damascus is a town in Washington County, Virginia, United States. Start off your visit on the 1st (Fri): hike along Virginia Creeper National Recreation Trail, then hike along Virginia Creeper Trail Club, and then see the interesting displays at Fields-Penn 1860 House Museum.

For where to stay, ratings, more things to do, and other tourist information, use the Damascus road trip app .

You can drive from Shenandoah National Park to Damascus in 4.5 hours. Another option is to do a combination of car and flight. In October, daily temperatures in Damascus can reach 69°F, while at night they dip to 49°F. Wrap up your sightseeing on the 1st (Fri) to allow time to travel to Charlottesville.

Things to do in Damascus

Outdoors Trails Parks

Side Trip

Abingdon
Find places to stay Oct 31 — Nov 1:
Highlights from your plan
Virginia Creeper Trail Club ©
Virginia Creeper Trail Club
Fields-Penn 1860 House Museum ©
Fields-Penn 1860 House Museum

4
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.
Venture out of the city with trips to Virginia Military Institute (in Lexington), James Madison's Montpelier (in Montpelier Station) and Frontier Culture Museum (in Staunton). There's much more to do: admire the natural beauty at Monticello, experience rural life at Carter Mountain Orchard, take an in-depth tour of Brownsburg Museum, and look for all kinds of wild species at Virginia Safari Park.

Start your trip to Charlottesville by creating a personalized itinerary on Inspirock.

Traveling by car from Damascus to Charlottesville takes 4 hours. Alternatively, you can do a combination of car and flight. In November, daytime highs in Charlottesville are 59°F, while nighttime lows are 37°F. Wrap up your sightseeing on the 5th (Tue) early enough to take a bus to Richmond.

Things to do in Charlottesville

Parks Historic Sites Wildlife

Side Trips

Appomattox Court House National Historical Park, Virginia Military Institute, National D-Day Memorial, Virginia Safari Park, Thomas Jefferson's Poplar Forest
Find places to stay Nov 1 — 5:
Highlights from your plan
National D-Day Memorial ©
National D-Day Memorial
Monticello ©
Monticello
Carter Mountain Orchard ©
Carter Mountain Orchard

4
nights
Richmond

Richmond ©
The capital city of Virginia, Richmond has diverse architecture, a large collection of monuments, and world-class museums that reveal the city's important role in American history.
You'll find plenty of places to visit near Richmond: Williamsburg (Jamestown Settlement, Historic Jamestowne, & more). Next up on the itinerary: admire the masterpieces at Virginia Museum of Fine Arts, explore the different monuments and memorials at Hollywood Cemetery, explore and take pictures at Maymont, and contemplate in the serene atmosphere at Blandford Church and Cemetery.

To find more things to do, ratings, and more tourist information, refer to the Richmond trip itinerary builder tool .

You can take a bus from Charlottesville to Richmond in 1.5 hours. Alternatively, you can drive. November in Richmond sees daily highs of 61°F and lows of 38°F at night. Cap off your sightseeing on the 9th (Sat) early enough to go by car to Chincoteague Island.

Things to do in Richmond

Historic Sites Museums Parks

Side Trips

Williamsburg, Blandford Church and Cemetery
Find places to stay Nov 5 — 9:
Highlights from your plan
Colonial Williamsburg ©
Colonial Williamsburg
Historic Jamestowne ©
Historic Jamestowne
Virginia Museum of Fine Arts ©
Virginia Museum of Fine Arts

4
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.
Chincoteague Island is known for nature, wildlife, museums, shopping, and historic sites. Your plan includes some of its best attractions: identify plant and animal life at Chincoteague National Wildlife Refuge, take an in-depth tour of Museum of Chincoteague, look for gifts at Pony Tails, and shop like a local with Tryfan Gallery.

To find maps, reviews, and more tourist information, refer to the Chincoteague Island day trip planning website .

You can drive from Richmond to Chincoteague Island in 4 hours. Alternatively, you can take a bus; or take a bus. In November, daily temperatures in Chincoteague Island can reach 59°F, while at night they dip to 40°F. Wrap up your sightseeing on the 13th (Wed) early enough to drive to Virginia Beach.

Things to do in Chincoteague Island

Parks Outdoors Wildlife

Side Trip

Chincoteague Bay Field Station
Find places to stay Nov 9 — 13:
Highlights from your plan
Chincoteague National Wildlife Refuge ©
Nature & Wildlife Tours
Museum of Chincoteague ©
Museum of Chincoteague

5
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: Busch Gardens Williamsburg (in Williamsburg), 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: take a leisurely stroll along Virginia Beach Boardwalk, take in the pleasant sights at King Neptune Statue on the Boardwalk, pause for some photo ops at Naval Aviation Monument, and explore the world behind art at Chrysler Museum of Art.

To see ratings, more things to do, maps, and tourist information, use the Virginia Beach online route planner .

You can drive from Chincoteague Island to Virginia Beach in 2.5 hours. Alternatively, you can take a bus; or take a bus. In November, daytime highs in Virginia Beach are 62°F, while nighttime lows are 43°F. Finish your sightseeing early on the 18th (Mon) so you can travel back home.

Things to do in Virginia Beach

Parks Museums Outdoors

Side Trips

Norfolk, Newport News, Smithfield, Busch Gardens Williamsburg, Old Point Comfort Lighthouse
Find places to stay Nov 13 — 18:
Highlights from your plan
St. Luke's Historic Church & Museum ©
Virginia Beach Boardwalk ©
Virginia Beach Boardwalk
Busch Gardens Williamsburg ©
Busch Gardens Williamsburg

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