I’m seriously attracted to historic hotels. The first inklings of a road trip can be stirred by a desire to stay in one. I peruse sites like the National Trust’s Historic Hotels, and Relais & Chateaux hoping to find places I haven’t yet stayed.

When it comes to Keswick Hall in Virginia, however, I’ve enjoyed its beauty and hospitality on many occasions and couldn’t resist returning once more as we began our adventure through the mid-Atlantic.

The pace of our road trip to Virginia was meant to be leisurely. We planned a few specific stops and decided we’d play the rest “by ear.” The apps on our iPhones would help us find any necessary non-destination hotels, as well as food and attractions along the way. We headed out on backroads. That’s our M.O.

We drove through mountains and National Forests, the more easterly and slower route, taking completely inefficient detours through Charlotte, NC for a good night’s sleep and a meal at The Dunhill Hotel, a smaller historic hotel, downtown. Then a half day in Hickory, NC for outlet furniture shopping. (They ship everywhere.)

We arrived at Keswick Hall in the evening, greeted by a warmly lit exterior and, in our room, chocolates, a full ice bucket and bottles of champagne and sparkling water.

Keswick Hall – a Virginia horse country version of Downton Abbey – was once owned by the widower of British designer Laura Ashley. Sir Bernard Ashley filled it with the faded English country house florals and chintzes you would expect. There were soft couches next to fireplaces and a cozy mix of patterns in the cushions and window treatments.

The resort sits on 600 acres, with a classic country-house style pool. There are loads of antique shops, restaurants and attractions nearby. Of course, some of America’s oldest house museums are in the neighborhood, too. There’s Thomas Jefferson’s Monticello, a personal favorite.

In summer you’ll find Jefferson’s gardens in full bloom. Make sure to tour Mulberry Row at Monticello, where the Hemmings family lived, along with over 400 other enslaved laborers. A 20-minute guided presentation offers unique insights into slave life at Monticello. You can also book a behind-the-scenes tour that provides access to the private second and third floors of Monticello.

We also made stops at the historic homes of James Madison and James Monroe. Dolly Madison’s inauguration gown and other costumes prove she was the Jackie O. of her generation.

Then we headed out, on a whim, towards Washington, DC.

The museums of the Smithsonian are always a good stop. We enjoyed a tour of The Butterfly Pavilion on this trip. (Versions of my butterfly photos eventually ended up as SmithHönig patterns!)

Yes, our Bisnagar Stripe fabric has a layer of butterflies underneath all that texture! We also created a line of Bisnager place mats in another colorway, adding pops of color to the table or those road trip picnics

From Washington, DC, we kept driving. Off track and off schedule, we just couldn’t resist.

We headed up the road towards Pennsylvania, where we managed to book two nights at the Rittenhouse Hotel, a luxe boutique hotel on Rittenhouse Square.

Among the many attributes of The Rittenhouse, their afternoon teas and over-the-top weekend brunches rank pretty high. The location is perfect, too. Surrounding Rittenhouse Square are numerous cafes. Many attractions are within walking distance, and the square itself offers people watching and beautiful statuary.

We visited the Rodin Museum and the Philadelphia Museum of Art, as well.

And then we backtracked to Longwood Gardens in Pennsylvania for a leisurely meander through the topiary. We were (sort of, maybe, slightly) headed home.

Of course, we had to enjoy a few picnics along the way. My favorite, on the road, is to stop at a local market or grocery store and pick up fruit, bread, pickles, cheese – and perhaps some regional delicacies or premade deli salads.

We find a picnic area – or sometimes just a green spot in a park – along the way. We open up the back of the car, or spread out on the ground.

I admit to keeping metal plates, flatware, a bottle opener, corkscrew, knife, and cloth napkins in a small, zip up picnic pouch in the car. There’s another container holding zip up storage bags, cups, and more. (I also keep swimsuits and towels in the car, a trick I learned living in Southern California. You never know when you might find time for a swim – or a picnic!)

It was during an impromptu late afternoon picnic that the idea came to us…

What if we didn’t drive home!?! Yes, there was work to be done. Work that couldn’t be done from the road. But what if we parked the car and came back to it in a few weeks?

The idea of what would eventually become our Progressive Road Trip – a 19,000 mile trek across America, on back roads and byways – was born.

At the time we had no idea what it would turn into, or how many miles we would travel. But we booked a last minute flight from Baltimore-Washington International Airport and parked in the cheapest long-term airport parking we could find. The vague formation of a plan was developing.

Summer was still in front of us and we’d get back to the Lincoln in a few weeks…

Shop our favorite road trip picnic selections here.

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