57 days in Virginia Itinerary

57 days in Virginia Itinerary

Created using Inspirock Virginia sightseeing planner

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Route & dates

57 days in Virginia Itinerary

Start: Montreal
Fly + taxi:  5​h 30​min
1
Chincoteague Island
— 5 nights
Drive:  2​h 30​min
2
Virginia Beach
— 6 nights
Drive:  1​h 15​min
3
Williamsburg
— 7 nights
Drive:  2​h 15​min
4
Charlottesville
— 6 nights
Drive:  1​h 15​min
5
Lexington
— 6 nights
Drive:  2​h 45​min
6
Damascus
— 2 nights
Drive:  4​h 15​min
7
Shenandoah National Park
— 6 nights
Drive:  1​h 15​min
8
Luray
— 6 nights
Drive:  1​h 15​min
9
Winchester
— 6 nights
Drive:  1​h 45​min
10
Alexandria
— 6 nights
Fly:  4​h 30​min
End: Montreal

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.
Change things up with these side-trips from Chincoteague Island: Onancock (Ker Place & Hopkins & Bros. Store). There's lots more to do: explore the striking landscape of Chincoteague National Wildlife Refuge, walk around Chincoteague Veteran's Memorial Park, surround yourself with nature on a nature and wildlife tour, and stop by MamerSass.

To find reviews, maps, more things to do, and tourist information, read our Chincoteague Island sightseeing planner .

Montreal, Canada to Chincoteague Island is an approximately 5.5-hour combination of flight and taxi. You can also do a combination of flight, bus, and taxi; or drive. Plan for somewhat warmer temperatures traveling from Montreal in October, with highs in Chincoteague Island at 25°C and lows at 14°C. Wrap up your sightseeing on the 17th (Thu) early enough to drive to Virginia Beach.

Things to do in Chincoteague Island

Parks Wildlife Outdoors

Side Trips

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

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.
You'll find plenty of places to visit near Virginia Beach: Chesapeake Bay Bridge-Tunnel (in Cape Charles), Weyanoke Bird and Wildflower Sanctuary (in Norfolk) and Old Point Comfort Lighthouse (in Hampton). The adventure continues: take in the waterfront at Virginia Beach Boardwalk, enjoy the sand and surf at Sandbridge Beach, explore the world behind art at Chrysler Museum of Art, and brush up on your knowledge of spirits at Tarnished Truth Distilling Company.

To see photos, traveler tips, maps, and tourist information, use the Virginia Beach online trip itinerary planner .

You can drive from Chincoteague Island to Virginia Beach in 2.5 hours. Other options are to take a bus; or take a bus. In October, daytime highs in Virginia Beach are 27°C, while nighttime lows are 15°C. Finish your sightseeing early on the 23rd (Wed) so you can drive to Williamsburg.

Things to do in Virginia Beach

Parks Museums Outdoors

Side Trips

Norfolk, Chesapeake Bay Bridge-Tunnel, Old Point Comfort Lighthouse
Highlights from your plan
Tarnished Truth Distilling Company ©
Virginia Beach Boardwalk ©
Virginia Beach Boardwalk
Military Aviation Museum ©
Military Aviation Museum

7
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.
Get out of town with these interesting Williamsburg side-trips: Newport News (The Mariners' Museum & Park & The Noland Trail), Smithfield (St. Luke's Historic Church & Museum & Windsor Castle Park) and Richmond (Bill Bojangles Robinson Monument, Virginia Museum of Fine Arts, & more). Next up on the itinerary: steep yourself in history at Colonial Williamsburg, take in the architecture and atmosphere at Bruton Parish Episcopal Church, explore the wealth of natural beauty at Colonial National Historical Park, and step aboard Jamestown Settlement.

To see reviews, maps, ratings, and tourist information, use the Williamsburg trip itinerary builder site .

Getting from Virginia Beach to Williamsburg by car takes about 1.5 hours. Other options: take a bus; or take a bus. In October, daytime highs in Williamsburg are 28°C, while nighttime lows are 15°C. Wrap up your sightseeing on the 30th (Wed) early enough to drive to Charlottesville.

Things to do in Williamsburg

Historic Sites Museums Parks

Side Trips

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

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: Bold Rock Hard Cider (in Nellysford), James Madison's Montpelier (in Montpelier Station) and The Quarry Gardens (in Schuyler). The adventure continues: admire the natural beauty at Monticello, gain insight at University of Virginia, get outside with Cavalier Sporting Clays, and experience rural life at Carter Mountain Orchard.

For maps, traveler tips, where to stay, and tourist information, use the Charlottesville road trip website .

You can drive from Williamsburg to Charlottesville in 2.5 hours. Another option is to take a bus. Traveling from Williamsburg in October, you can expect nighttime temperatures to be a bit cooler in Charlottesville, with lows of 11°C. Cap off your sightseeing on the 5th (Tue) early enough to go by car to Lexington.

Things to do in Charlottesville

Parks Outdoors Trails

Side Trips

Staunton, The Quarry Gardens, Fluvanna Heritage Trail, Cavalier Sporting Clays, Open Gate Farm
Highlights from your plan
Monticello ©
Monticello
Carter Mountain Orchard ©
Carter Mountain Orchard
University of Virginia ©
University of Virginia

6
nights
Lexington

Lexington ©
Home to two prestigious educational institutions, Lexington was founded in 1778.
You'll find plenty of places to visit near Lexington: Roanoke (Beer Tastings & Tours & Mill Mountain Star & Park), National D-Day Memorial (in Bedford) and Lynchburg (Blackwater Creek Trail, Room Escape Games, & more). There's lots more to do: gain insight at Virginia Military Institute, identify plant and animal life at Virginia Safari Park, steep yourself in history at Lee Chapel and Museum, and join the crowd at Martinsville Speedway.

To see more things to do, photos, maps, and more tourist information, you can read our Lexington tour itinerary tool .

Traveling by car from Charlottesville to Lexington takes 1.5 hours. Alternatively, you can do a combination of train and taxi. When traveling from Charlottesville in November, plan for little chillier days and about the same nights in Lexington: temperatures range from 10°C by day to 0°C at night. Cap off your sightseeing on the 11th (Mon) early enough to travel to Damascus.

Things to do in Lexington

Parks Historic Sites Wildlife

Side Trips

Lynchburg, Natural Bridge, Roanoke, National D-Day Memorial, Martinsville Speedway
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

2
nights
Damascus

Damascus ©
Damascus is a town in Washington County, Virginia, United States. On the 12th (Tue), trek along Virginia Creeper National Recreation Trail, immerse yourself in nature at Grayson Highlands State Park, and then tour the pleasant surroundings at Appalachian Trail. Here are some ideas for day two: explore the striking landscape at The Channels Natural Area Preserve and then get engrossed in the history at The Birthplace of Country Music Museum.

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

You can drive from Lexington to Damascus in 3 hours. Traveling from Lexington in November, expect nights in Damascus to be about the same, around 3°C, while days are a bit warmer, around 16°C. Wrap up your sightseeing on the 13th (Wed) to allow time to travel to Shenandoah National Park.

Things to do in Damascus

Parks Trails Outdoors

Side Trips

The Channels Natural Area Preserve, Grayson Highlands State Park, Appalachian Trail, The Birthplace of Country Music Museum
Highlights from your plan
Grayson Highlands State Park ©
Grayson Highlands State Park

6
nights
Shenandoah National Park

Shenandoah National Park ©
Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.
Change things up with these side-trips from Shenandoah National Park: Grand Caverns (in Grottoes), Brix and Columns Vineyards (in McGaheysville) and SoLace Studios Fine Handcrafts (in Elkton). And it doesn't end there: explore and take pictures at Skyline Drive, take in the awesome beauty at Pinnacles, hike along Appalachian Trail, and admire the sheer force of Dark Hollow Falls.

To find maps, photos, other places to visit, and tourist information, use the Shenandoah National Park trip planning app .

Traveling by car from Damascus to Shenandoah National Park takes 4.5 hours. Alternatively, you can do a combination of car and flight. Expect a daytime high around 17°C in November, and nighttime lows around 3°C. Finish up your sightseeing early on the 19th (Tue) so you can go by car to Luray.

Things to do in Shenandoah National Park

Parks Outdoors Nature

Side Trips

Harrisonburg, Grand Caverns, Brix and Columns Vineyards, Mt. Crawford Creamery, SoLace Studios Fine Handcrafts
Highlights from your plan
Old Rag Mountain Hike ©
Old Rag Mountain Hike
Skyline Drive ©
Skyline Drive
Appalachian Trail ©
Appalachian Trail

6
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 the numerous day-trip ideas around Luray: Culpeper (Museum of Culpeper History & Moving Meadows Farm), Front Royal (Blue Ridge Hospice Thrift Shop & Buzzard Rock North) and Shenandoah Valley Cultural Heritage Museum at The Edinburg Mill (in Edinburg). And it doesn't end there: take in breathtaking views at Luray Caverns, trek along Kennedy Peak Hike, tour the pleasant surroundings at Whiteoak Canyon Falls, and Head underground at Shenandoah Caverns.

To see reviews, photos, other places to visit, and tourist information, you can read our Luray trip planner .

Traveling by car from Shenandoah National Park to Luray takes 1.5 hours. Expect a daytime high around 16°C in November, and nighttime lows around 1°C. Cap off your sightseeing on the 25th (Mon) early enough to go by car to Winchester.

Things to do in Luray

Parks Outdoors Trails

Side Trips

Front Royal, Culpeper, Sperryville, New Market State Historical Park, 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

6
nights
Winchester

Winchester ©
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Explore Winchester's surroundings by going to Glenwood Park (in Middleburg), Bluemont (Raven Rocks & Wild Hare Hard Cider) and Leesburg (Ida Lee Park, Audubon Naturalist Society Rust Nature Sanctuary, & more). There's still lots to do: wander the wide-open spaces of Rocking S Ranch, immerse yourself in nature at Sky Meadows State Park, walk around Sherando Park, and identify plant and animal life at Blue Ridge Center for Environmental Stewardship.

To find traveler tips, where to stay, other places to visit, and tourist information, use the Winchester trip maker app .

Drive from Luray to Winchester in 1.5 hours. In November, daily temperatures in Winchester can reach 14°C, while at night they dip to 1°C. Finish your sightseeing early on the 1st (Sun) so you can drive to Alexandria.

Things to do in Winchester

Parks Outdoors Nature

Side Trips

Leesburg, Purcellville, Bluemont, Royal Horseshoe Farm, Sky Meadows State Park
Highlights from your plan
Rocking S Ranch ©
Rocking S Ranch
Cascade Falls ©
Cascade Falls
Raven Rocks ©
Raven Rocks

6
nights
Alexandria

Alexandria ©
Just a few metro stops away from the bustle of Washington D.C., Alexandria provides a respite from the fast-paced capital.
You'll find plenty of places to visit near Alexandria: Aslin Brewery (in Herndon), Quantico National Cemetery (in Quantico) and National Museum of the Marine Corps (in Triangle). There's much more to do: contemplate the long history of Arlington National Cemetery, examine the collection at Steven F. Udvar-Hazy Center, pause for some photo ops at Pentagon Memorial, and stroll through Mount Vernon Trail.

To see more things to do, where to stay, other places to visit, and more tourist information, use the Alexandria trip itinerary planner .

Drive from Winchester to Alexandria in 2 hours. Alternatively, you can take a train; or take a bus. Expect somewhat warmer evenings in Alexandria when traveling from Winchester in December, with lows around 3°C. Finish your sightseeing early on the 7th (Sat) to allow enough time to travel back home.

Things to do in Alexandria

Historic Sites Parks Museums

Side Trips

Arlington, Manassas, Quantico National Cemetery, Aslin Brewery, George Washington's Mount Vernon
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

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