Scenic Backroads to Pittsburgh

  • Scenic Backroads
  • Laurel Highlands south of Pittsburgh
  • Frank Lloyd Wright’s Fallingwater


May 19 - 25, 2024


  • Lovely boutique inns
  • Guided tour of Pittsburgh’s steel heritage by riverboat and high-roofed van
  • Other Pittsburgh stops: the Vanka Murals, the Mt. Washington inclines, Squirrel Hill, and the Henry Clay Frick estate
  • Fallingwater, the National Road, and West Virginia’s Canaan Valley

Trip Description

Join us for our second pilgrimage to Pittsburgh—stunning in its stories of interest and wealth of knowledge from great guides to help us in our explorations there.  And Pittsburgh is just one part of the outstanding trifecta of facets to this adventure. We will also explore the beautiful “Laurel Highlands” south of the city, featuring places like Frank Lloyd Wright’s Fallingwater (house / estate), and we’ll delve into some of eastern America’s prettiest drives and beautiful geography on our “small roads drives” through Virginia and West Virginia—on both ends of the trip.

Mountain towns, with interesting stories? The prominent, striking geography of the Appalachian Ridge and Valley region? Urban stories – on both sides of the “industrial divide?” Frank Lloyd Wright and the melding of natural features into retreat living? Come exploring with us, on our “Scenic Backroads to Pittsburgh” expedition… and learn the meaning of slow travel, while discovering places and stories hidden in the Allegheny mist. Let’s hop!



Sunday, May 19

We depart the western Carolinas this morning, for a steady drive north: Destination, Lexington, Virginia. Though we’re “covering ground,” the geography is magnificent: We’ll ascend the Appalachian Escarpment, enter the basin of the New River, then finally arrive in lovely Lexington.

Our accommodation for the night is the Hampton Inn-Lexington Historic District, built on the grounds of the historic Col Alto Mansion. Rest, Relax… enjoy an optional stroll downtown, or in the adjacent residential neighborhood.

Dinner and overnight, Lexington, Virginia.

Monday, May 20

Breakfast in the inn; then departure. Before leaving Lexington, itself, we’ll enjoy a driving tour of Washington and Lee University, and Virginia Military Institute. We’ll make a stop at the VMI Museum; and we’ll visit the Newmarket Cadet Memorial nearby.

Our driving route will take us into the folded landscape of the Appalachian Ridge and Valley: ridges that extend for 100 miles or more, mirroring each other and flanking our driving route. Valleys of thriving, historic farms – and important rivers, like the South Fork of the Potomac. We’ll drive through the pretty towns of Monterrey, Virginia; and Franklin, West Virginia. We’ll see the stunning Seneca Rocks formation; and we’ll finally alight in one of America’s finest valleys: crater-like Canaan Valley.

Dinner and overnight at the Canaan Resort.

Tuesday, May 21

Enjoy a delicious cooked breakfast this morning; then we’re off.

Canaan Valley and the nearby towns of Davis and Thomas, WV, represent some of the highest inhabited terrain in the eastern U.S. Davis measures just under 3600’ and parts of “the Valley” top 4000’. [In fact, only a handful of “sky-high” NC towns exceed those lofty measurements, with Highlands, NC, soaring to 4200’.] Our driving route will take us through both Davis and Thomas – and then make a brief and short detour to view the Fairfax Stone. Turns out, we’re not the first explorers in these parts! In the year 1737, one Lord Fairfax, who figured he owned just about everything in every direction, made an effort to discover the ultimate “source” of the Potomac River (… that is, what we now call the Northern Branch of the Potomac River). That “source” lies just off the southwestern corner of Maryland, in West Virginia – marked by Fairfax with a large stone.

We’ll continue our drive through lovely Western Maryland, where we’ll briefly follow the route of America’s first National Road – that connected Cumberland, Maryland, to Wheeling, Virginia (we’ll straighten the geography out on our trip).

In the afternoon, we’ll arrive in Pittsburgh. We’ll enjoy a good local lunch, with a million dollar view. Then we’ll descend to water level, for a lovely narrated excursion on Pittsburgh’s Three Rivers.

Later in the afternoon, we’ll check into our lodging for the next two nights: The Mansions on Fifth Hotel.

Dinner and overnight, Pittsburgh.

Wednesday, May 22

Enjoy breakfast in the inn. Then, let’s explore!

Today’s adventure will include a driving tour of Homestead – the steel factory town that Andrew Carnegie built; and a guided tour of the Carrie Blast Furnace. We’ll learn the story of steel: the good, the bad, and the ugly.

We’ll also visit Squirrel Hill – Pittsburgh’s suburban high ground: the chosen home of the Gilded Age “captains” of Pittsburgh’s industry. A highlight will be a tour of Clayton – home of Henry Clay Frick, President of Carnegie Steel, notorious “breaker” of the Homestead Strike, and collector of commodities that matched his disposable wealth.

Dinner and overnight, Pittsburgh.

Thursday, May 23

We’ll rise to the smell of a delicious breakfast, once more (could one get used to this?).

Then we’ll pay a visit to the St. Nicholas Catholic Church: home of the Vanka Murals. The fresco paintings – produced by Croatian-born Maxo Vanka in 1937 and 1941 – are shocking in their head-on treatment of “war,” “capitalism,” and other present-day social dysfunctions. We’ll enjoy a short, guided presentation.

Then we’ll depart the Steel City, following a lovely driving route into the Laurel Highlands, southeast of the city. We’ll visit one of the most storied residences in the U.S. – Fallingwater, produced by modernist, Frank Lloyd Wright in the 1930’s for Pittsburgh department store magnate, Edgar Kaufmann.

We’ll make our way to our lovely bed and breakfast accommodation for the night, the Hartzell House, located along part of the old National Road, just north of the Maryland boundary. Dinner and overnight, Addison, PA.

Friday, May 24

After breakfast, we’ll bid adieu to our kind hosts. Then we’ll drive through Cumberland, MD, en route to Berkeley Springs – favored by George Washington and some of his contemporaries, for the mineral waters and baths. We’ll enjoy lunch in this scenic area, then drive into Virginia, and on to our accommodation for the last night of our trip – The Blackburn Inn, in Staunton, Virginia. (We’ll tell the story of the acclaimed Blackburn Inn on location.)

Dinner and overnight, Staunton, VA.

Saturday, May 25

Breakfast, then off we go. We’ll drive scenic Interstate 81 south to Marion, VA, then stop for lunch.

We’ll arrive back home in the late-afternoon.

Featured Experiences

Canaan Valley Resort

Canaan Valley Resort and Conference Center is a West Virginia state park that provides the perfect year-round destination for individuals of all ages. Immerse yourself in the natural beauty and tranquility of your surroundings while indulging in all of the fine amenities and adventures the area has to offer.

Hartzell House Bed & Breakfast

A casually luxurious 7000-square-foot B&B in Addison, PA. It is a handsome example of Carpenter Gothic Victorian fused seamlessly with Craftsman style. Our lodging accommodations are comfortably appointed throughout with furnishings chosen to pamper and please our discerning guests, and we have added high quality, HEPA air filters to all common areas and guest rooms for extra peace of mind. In the historic West Wing, originally built by Judson Hartzell c1870, the original structure has been carefully renovated and expanded to retain the flavor of the era, while enhancing the measure of technical necessity and environmental comfort.

The Blackburn Inn

A Remarkable Stay
Rich in history and steeped in elegant charm, The Blackburn Inn and Conference Center is located just steps from Downtown Staunton on more than eighty acres of rolling Virginia hills. This special property is at once awe-inspiring and intimate, with event and conference venues unlike any other in the Shenandoah Valley.

What's Included

  • Comfortable high-roofed van transportation
  • Accommodation for 6 nights with breakfast in a variety of high-standard inns / hotels
  • 5 lunches and 4 dinners
  • All activities/admissions per the itinerary
  • Guide and concierge service throughout the trip

Trip Price

$3,941 / person (double occupancy; single supplement, $695)

What's Not Included

Price does not include alcohol, other meals, or trip insurance (recommended).

Couldn't have asked for more in terms of weather, accommodations and scenery. Can't wait to go on another adventure with Explore Up Close!
My husband and I love the attention to detail. We always have a wonderful experience: visiting new and interesting places, eating lots of good food, making new friends, and exploring new places!

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