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AI-VascoDaGama
12 Jun 2026Updated last time
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Pennsylvania to Virginia Road Trip Itinerary

Pennsylvania to Virginia Road Trip Itinerary Overview

This road trip from Pennsylvania to Virginia offers a rich mix of American history, scenic mountain landscapes, underground natural wonders, and coastal relaxation. Start with meaningful stops at Gettysburg National Military Park and Antietam National Battlefield, where preserved grounds, monuments, and visitor centers provide powerful insight into pivotal Civil War events. From there, transition into the beauty of Shenandoah National Park, where Skyline Drive delivers panoramic Blue Ridge vistas, hiking opportunities, and memorable overlooks ideal for photos and quiet breaks. Continue to Luray Caverns for a striking change of scenery, exploring dramatic rock formations and one of the East Coast’s most famous cave systems.

As the trip continues, Virginia’s historical depth becomes even more apparent with visits to Monticello and Mount Vernon, where the homes of Thomas Jefferson and George Washington reveal architecture, landscape design, and the complexities of early American life. In Jamestown, the story of the first permanent English settlement adds another foundational chapter to the journey. Balance these reflective and educational experiences with time at the Virginia Beach Boardwalk, where ocean views, entertainment, and a lively promenade create a more relaxed atmosphere. Finally, end with powerful national landmarks at Arlington National Cemetery and the National Mall in Washington, D.C., tying together themes of sacrifice, identity, and civic memory. Altogether, this itinerary is ideal for travelers who want a well-rounded drive filled with history, nature, culture, and classic East Coast experiences.

Recommended Activities

  • Trip Point Pin1

    Gettysburg National Military Park

    Gettysburg is a pivotal Civil War site where the 1863 battle and Lincoln’s Gettysburg Address significantly shaped U.S. history. Visitors can explore expansive preserved battlefield landscapes, detailed interpretive exhibits at the Visitor Center and Museum, guided ranger programs, and driving tours with marked battle lines that bring key moments and tactics to life. It’s essential for history, remembrance, and understanding the conflict’s human and national impact.
    Gettysburg National Military Park
    Gettysburg National Military Park
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    Gettysburg National Military Park
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    Gettysburg National Military Park
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    Gettysburg National Military Park
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  • Trip Point Pin2

    Antietam National Battlefield

    Antietam is the site of the single bloodiest day in American military history (September 17, 1862). The park preserves battlefield terrain, monuments, and an informative visitor center with exhibits and walking trails that illustrate troop movements and personal stories. Visiting offers a powerful, somber reflection on the costs of war and insight into why the battle influenced the course of the Civil War and President Lincoln’s decision to issue the preliminary Emancipation Proclamation.
    Antietam National Battlefield
    Antietam National Battlefield
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    Antietam National Battlefield
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    Antietam National Battlefield
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    Antietam National Battlefield
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  • Trip Point Pin3

    Shenandoah National Park - Skyline Drive

    Skyline Drive offers stunning, accessible scenic driving along the crest of the Blue Ridge Mountains with panoramic overlooks, abundant fall foliage, and abundant wildlife viewing. The park provides countless hiking trails (including access to sections of the Appalachian Trail), waterfalls, picnic areas, and backcountry camping. It’s ideal for outdoor recreation, photography, and peaceful immersion in nature within short driving distance from many mid-Atlantic population centers.
    Shenandoah National Park - Skyline Drive
    Shenandoah National Park - Skyline Drive
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    Shenandoah National Park - Skyline Drive
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    Shenandoah National Park - Skyline Drive
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    Shenandoah National Park - Skyline Drive
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  • Trip Point Pin4

    Luray Caverns

    Luray Caverns features spectacular underground limestone formations—tall stalactites, stalagmites, mirrored pools, and the Great Stalacpipe Organ (an instrument that produces tones from the cave’s formations). Guided tours are accessible to most visitors and highlight geology, cave history, and unique formations; the caverns offer a cool, otherworldly experience and excellent photo opportunities.
    Luray Caverns
    Luray Caverns
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    Luray Caverns
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    Luray Caverns
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    Luray Caverns
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    Luray Caverns
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    Luray Caverns
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  • Trip Point Pin5

    Monticello

    Monticello, Thomas Jefferson’s plantation and architectural masterpiece, offers insight into Jefferson’s life, ideas, and innovations. The house tour showcases original rooms, design features, and artifacts; the estate includes restored gardens, a working farm, and exhibits addressing the complexities of Jefferson’s legacy, including slavery. It’s essential for understanding early American history, architecture, and Enlightenment-era thought.
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  • Trip Point Pin6

    Mount Vernon

    Mount Vernon, George Washington’s preserved estate on the Potomac River, provides a vivid portrait of the first U.S. president’s private and public life. The mansion, outbuildings, gardens, and working farm are interpreted through guided tours, period rooms, and engaging exhibits that cover Washington’s leadership, estate management, and the lives of the enslaved community. The riverside setting and living-history demonstrations make it both educational and evocative.
    Mount Vernon
    Mount Vernon
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    Mount Vernon
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    Mount Vernon
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    Mount Vernon
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  • Trip Point Pin7

    Colonial National Historical Park - Jamestown

    Jamestown marks the first permanent English settlement in North America (1607) and is foundational to U.S. colonial history. The park’s archaeological sites, reconstructed fort areas, and the Jamestown Settlement living-history museum interpret early colonial life, Native American interactions, and the challenges of survival. Visiting provides direct insight into early colonial governance, trade, and the cultural encounters that shaped subsequent American history.
    Colonial National Historical Park - Jamestown
    Colonial National Historical Park - Jamestown
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    Colonial National Historical Park - Jamestown
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    Colonial National Historical Park - Jamestown
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    Colonial National Historical Park - Jamestown
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  • Trip Point Pin8

    Virginia Beach Boardwalk

    The Virginia Beach Boardwalk is a lively oceanfront promenade offering wide sandy beaches, scenic views of the Atlantic, public art, recreational facilities, and year-round events. It’s ideal for sunbathing, swimming, biking, people-watching, and enjoying nearby shops, cafes, and attractions such as the Neptune statue and outdoor concerts—making it a classic seaside destination for relaxation and family fun.
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  • Trip Point Pin9

    Arlington National Cemetery

    Arlington National Cemetery is a solemn national military cemetery honoring U.S. service members and notable figures. Key sites include the Tomb of the Unknown Soldier with its changing of the guard, the John F. Kennedy Eternal Flame, and numerous memorials and unit gravesites. Visiting offers a moving, reflective experience that honors sacrifice, provides historical context across conflicts, and connects visitors to national remembrance traditions.
    Arlington National Cemetery
    Arlington National Cemetery
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    Arlington National Cemetery
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    Arlington National Cemetery
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    Arlington National Cemetery
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  • Trip Point Pin10

    National Mall and Memorial Parks (Washington, D.C.)

    The National Mall is the symbolic and physical heart of the nation, featuring iconic monuments and memorials—Lincoln Memorial, Washington Monument, World War II, Vietnam Veterans, and more—set among expansive green spaces and Smithsonian museums. Visiting offers a concentrated, powerful experience of U.S. history, civic identity, and public memory; it provides excellent photo ops, free world-class museums, interpretive programs, and easy walking connections between major cultural and governmental sites.
    National Mall and Memorial Parks (Washington, D.C.)
    National Mall and Memorial Parks (Washington, D.C.)
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    National Mall and Memorial Parks (Washington, D.C.)
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    National Mall and Memorial Parks (Washington, D.C.)
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    National Mall and Memorial Parks (Washington, D.C.)
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Restaurants

  • Restaurant Icon

    Bluebird Restaurant (Charlottesville, VA)

    5

    Bluebird Restaurant (Charlottesville, VA)

    Renowned for seasonal, ingredient-driven New American cuisine and a thoughtful wine list—great stop near Monticello for a refined farm-to-table meal.
    5
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    L'Auberge Chez François (Great Falls, VA)

    4.8
    $$$$

    L'Auberge Chez François (Great Falls, VA)

    Classic French-inspired dining in an elegant country inn setting—excellent for a special dinner stop while visiting Mount Vernon or heading toward DC.
    4.8
    $$$$
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    Central Restaurant & Bar (Charlottesville, VA)

    4.4
    $$$$

    Central Restaurant & Bar (Charlottesville, VA)

    Local favorite offering contemporary American dishes highlighting regional produce—convenient and well-regarded for visitors touring Monticello and the surrounding wineries.
    4.4
    $$$$
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    The Shack (Luray, VA)

    4.4
    $$$$

    The Shack (Luray, VA)

    Casual, popular spot near Luray Caverns serving American comfort food and craft beers—ideal for a relaxed meal after exploring the caverns.
    4.4
    $$$$
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    The Atlantic (Virginia Beach, VA)

    4.6
    $$$$

    The Atlantic (Virginia Beach, VA)

    Upscale seafood-focused restaurant with ocean views and a modern coastal menu—perfect for enjoying fresh regional seafood on the Virginia Beach waterfront.
    4.6
    $$$$
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Hotels

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    The Inn at Willow Grove (Orange, VA)

    4.6

    The Inn at Willow Grove (Orange, VA)

    Historic country inn near Monticello offering luxurious rooms, manicured grounds, fine dining, and easy access to Charlottesville wineries and Jeffersonian sites.
    4.6
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    Hotel Madison & Shenandoah Conference Center (Harrisonburg, VA)

    4.3

    Hotel Madison & Shenandoah Conference Center (Harrisonburg, VA)

    Comfortable, well-located hotel for exploring Shenandoah National Park and Luray Caverns; offers modern amenities and convenient access to Skyline Drive approaches.
    4.3
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    The Mimslyn Inn (Luray, VA)

    4.2

    The Mimslyn Inn (Luray, VA)

    Classic historic hotel in downtown Luray with elegant rooms and close proximity to Luray Caverns and Shenandoah Valley attractions—good for a charming, walkable stay.
    4.2
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    Hilton Garden Inn Charlottesville/UVA (Charlottesville, VA)

    4.3

    Hilton Garden Inn Charlottesville/UVA (Charlottesville, VA)

    Reliable mid-range option near the University of Virginia and Monticello with comfortable rooms, on-site dining, and convenient location for sightseeing.
    4.3
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    The Cavalier Virginia Beach (Virginia Beach, VA)

    4.6

    The Cavalier Virginia Beach (Virginia Beach, VA)

    Iconic luxury beachfront hotel with restored 1920s elegance, ocean views, upscale dining, and easy access to the Virginia Beach Boardwalk and waterfront attractions.
    4.6
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Local Events & Happenings

  • Event Icon

    MGK: Lost Americana Tour

    MGK: Lost Americana Tour

    GA PIT is STANDING ROOM ONLY. There are no seats in the GA PIT for this show. The GA PIT is general admission
    Map IconJiffy Lube Live in Bristow (20.87 mi)
    Calendar Icon3 Jun 2026
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  • Event Icon

    Forrest Frank: The Jesus Generation Tour

    Forrest Frank: The Jesus Generation Tour

    GRAMMY-nominated and GMA DOVE Award-winning artist FORREST FRANK has announced The Jesus Generation Tour with special guests Tori Kelly, Cory Asbury and The Figs. Presented by TPR and hitting 29 cities across the U.S., The Jesus Generation Tour follo...
    Map IconJiffy Lube Live in Bristow (20.87 mi)
    Calendar Icon12 Jun 2026
    Website IconVisit Website
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  • Event Icon

    Evanescence 2026 World Tour with Spiritbox and Nova Twins

    Evanescence 2026 World Tour with Spiritbox and Nova Twins

    Evanescence has partnered with PLUS1 so that $1 from every ticket sold will be donated by Live Nation to PLUS1 to support organizations providing humanitarian aid and medical relief to those in need around the world. No portion of the ticket purchase...
    Map IconJiffy Lube Live in Bristow (20.87 mi)
    Calendar Icon27 Jun 2026
    Website IconVisit Website
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  • Event Icon

    Chicago & Styx: The Windy Cities Tour

    Chicago & Styx: The Windy Cities Tour

    The event will take place at Jiffy Lube Live in Bristow.
    Map IconJiffy Lube Live in Bristow (20.87 mi)
    Calendar Icon20 Jul 2026
    Website IconVisit Website
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  • Event Icon

    Lynyrd Skynyrd x Foreigner: Double Trouble Double Vision Tour

    Lynyrd Skynyrd x Foreigner: Double Trouble Double Vision Tour

    PLEASE NOTE EVENT IS RAIN OR SHINE.
    Map IconJiffy Lube Live in Bristow (20.87 mi)
    Calendar Icon25 Jul 2026
    Website IconVisit Website
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  • Event Icon

    The Return Of The Carnival Of Sins: Mötley Crüe

    The Return Of The Carnival Of Sins: Mötley Crüe

    The event will take place at Jiffy Lube Live in Bristow.
    Map IconJiffy Lube Live in Bristow (20.87 mi)
    Calendar Icon3 Aug 2026
    Website IconVisit Website
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  • Event Icon

    Riley Green: Cowboy As It Gets Tour 2026

    Riley Green: Cowboy As It Gets Tour 2026

    GA PIT SECTION IS STANDING ROOM ONLY
    Map IconJiffy Lube Live in Bristow (20.87 mi)
    Calendar Icon8 Aug 2026
    Website IconVisit Website
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Travel Gems from Reddit

  • Reddit Icon

    Richmond, and Gettysburg has a lot of civil war history around it, downtown DC is great to walk around in (just park outside the city and take the metro in, parking in city is...

    Road trip from Pa to Virginia open to detours// fun suggestions

    Richmond, and Gettysburg has a lot of civil war history around it, downtown DC is great to walk around in (just park outside the city and take the metro in, parking in city is...

    /r/VirginiaBeach
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  • Reddit Icon

    Hi All, So, Im planning a trip to DC/Virginia with three of my friends for mid-March. Were leaving from Southeast PA (close to DE/MD borders) on

    Planning Virginia Trip (DC to Shenandoah Valley National Park)

    Hi All, So, Im planning a trip to DC/Virginia with three of my friends for mid-March. Were leaving from Southeast PA (close to DE/MD borders) on

    /r/Virginia
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  • Reddit Icon

    Looks like I could maybe stay in Staunton, pop over to Monticello in the AM, and then hit Skyline Dr between US-31 & US-211. My question - rhetorical - would then be could I d...

    Headed to Harrisburg, PA looking for recommendations en route. More info in comments.

    Looks like I could maybe stay in Staunton, pop over to Monticello in the AM, and then hit Skyline Dr between US-31 & US-211. My question - rhetorical - would then be could I d...

    /r/roadtrip
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  • Reddit Icon

    If you decide to go to Jamestown, bring LOTS of bug spray and sunscreen. The ships are really cool to explore. Head west on 64 and consider checking out Richmond or Charlottes...

    Virginia Road Trip

    If you decide to go to Jamestown, bring LOTS of bug spray and sunscreen. The ships are really cool to explore. Head west on 64 and consider checking out Richmond or Charlottes...

    /r/Virginia
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  • Reddit Icon

    Check out Rappahannock County, you should be able to find orchards on their sign. Sperryville is right over the mountain from Luray and they have great pizza and a few other r...

    Roadtrip Itinerary from Pittsburgh to Shenandoah

    Check out Rappahannock County, you should be able to find orchards on their sign. Sperryville is right over the mountain from Luray and they have great pizza and a few other r...

    /r/ShenandoahPark
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  • Reddit Icon

    Any portion of skyline drive you could take from around front royal or Luray down a ways, Luray Caverns, breweries or wineries or Carter Mountain Orchard around Charlottesvill...

    Driving from the North. Looking for road trip tips

    Any portion of skyline drive you could take from around front royal or Luray down a ways, Luray Caverns, breweries or wineries or Carter Mountain Orchard around Charlottesvill...

    /r/Virginia
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  • Reddit Icon

    The Shenandoah region of northern VA is great. You could drive Skyline Drive and visit Luray Caverns.

    Help with this leg!

    The Shenandoah region of northern VA is great. You could drive Skyline Drive and visit Luray Caverns.

    /r/roadtrip
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  • Reddit Icon

    If youre going to Harpers Ferry add Antietam. Others: Baltimore Inner Harbor, Ocean City, Skyline Drive, Luray Caverns, Charlottesville/Monticello, Colonial Williamsburg/Busch...

    Good road trips within 1-3 hours this time of year?

    If youre going to Harpers Ferry add Antietam. Others: Baltimore Inner Harbor, Ocean City, Skyline Drive, Luray Caverns, Charlottesville/Monticello, Colonial Williamsburg/Busch...

    /r/nova
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  • Reddit Icon

    189 votes, 313 comments. If you had one day, and could only pick one, which do you recommend? What other factors would you consider? We are going to

    If you could only pick one trip, for one day: Gettysburg or Valley Forge?

    189 votes, 313 comments. If you had one day, and could only pick one, which do you recommend? What other factors would you consider? We are going to

    /r/Pennsylvania
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  • Reddit Icon

    I went with my son's class on his 8th grade DC trip and we spent a day in Gettysburg. I'm not sure how to set it up, but we had an actual park tour guide get on the ...

    Recommended itinerary for a visit to Gettysburg

    I went with my son's class on his 8th grade DC trip and we spent a day in Gettysburg. I'm not sure how to set it up, but we had an actual park tour guide get on the ...

    /r/CIVILWAR
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  • Reddit Icon

    I do the trip to and from New Haven all the time.the western route through PA and Cumberland go[ avoids NYC but is longertake 84 through Danbury and cross the Hudson there.tim...

    Lower CT to VA for Shenandoah NP- which route and where to stop?

    I do the trip to and from New Haven all the time.the western route through PA and Cumberland go[ avoids NYC but is longertake 84 through Danbury and cross the Hudson there.tim...

    /r/roadtrip
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  • Reddit Icon

    I would suggest making Richmond your central location to stay, because everything is is basically 2 to 3 hours away from there, so you could leave at 9 and come back by 9, hit...

    7 Day Trip itinerary recommendations for Virginia & surrounding areas

    I would suggest making Richmond your central location to stay, because everything is is basically 2 to 3 hours away from there, so you could leave at 9 and come back by 9, hit...

    /r/Virginia
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  • Reddit Icon

    If you are driving from DC to Orlando or Savannah, or almost anywhere else South of DC, consider driving on Skyline Drive and the the Blue Ridge Parkway. They are beautiful fo...

    Advice for our East Coast USA Road Trip in January

    If you are driving from DC to Orlando or Savannah, or almost anywhere else South of DC, consider driving on Skyline Drive and the the Blue Ridge Parkway. They are beautiful fo...

    /r/usatravel
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  • Reddit Icon

    Planning to leave super early and come back late for a whole day! Interested in good eats (no meat), nature (no hiking), and/or paid excursions. Any

    Good day trip itinerary for luray/shanandoah?

    Planning to leave super early and come back late for a whole day! Interested in good eats (no meat), nature (no hiking), and/or paid excursions. Any

    /r/nova
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  • Reddit Icon

    I think Shenandoah is quite capable of giving you the same kind of experience. More replies More replies ... Yes. Ranger programs and some reasonable hikes (take a look at Sto...

    Is a trip to Shenandoah from NYC worth it?

    I think Shenandoah is quite capable of giving you the same kind of experience. More replies More replies ... Yes. Ranger programs and some reasonable hikes (take a look at Sto...

    /r/NationalPark
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  • Reddit Icon

    Hey guys, looking for suggestions for a fun road trip route. All young men, Open to route detours. ... The route you planned is a 1 day trip down, and 1 day trip back. So plea...

    Road-trip suggestions!!

    Hey guys, looking for suggestions for a fun road trip route. All young men, Open to route detours. ... The route you planned is a 1 day trip down, and 1 day trip back. So plea...

    /r/maryland
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  • Reddit Icon

    Day 1- PHI to Charlottesville/Monticello (avoid DC rush hour) Day 2- SNP to Lexington, Roanoke or peaks of Otter Day 3- Early departure to Asheville NC Day 4 - Asheville, Tabl...

    advice for VA, NC, SC, GA road trip

    Day 1- PHI to Charlottesville/Monticello (avoid DC rush hour) Day 2- SNP to Lexington, Roanoke or peaks of Otter Day 3- Early departure to Asheville NC Day 4 - Asheville, Tabl...

    /r/roadtrip
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  • Reddit Icon

    86 votes, 139 comments. I'm sure there are a bunch, but I can only think of some, so I'd love more suggestions. My mom is coming over to visit this

    Best daytrips or 2-day trips out of Pittsburgh?

    86 votes, 139 comments. I'm sure there are a bunch, but I can only think of some, so I'd love more suggestions. My mom is coming over to visit this

    /r/pittsburgh
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