Shenandoah Valley Tour Itinerary:

This is a tentative schedule - destinations and activities are subject to change

Day 1: Sunday

Relax, unwind and enjoy the amenities at the Hotel Roanoke or hop right into the historic downtown area, see the sights, and maybe even do some shopping in the market square. Whatever you choose, make sure you stop by the lobby to see us at the registration table to get what you’ll need for the week’s adventures.

After everyone has a chance to unpack and freshen up, we’ll head to our welcome cocktail reception and dinner on the hotel’s patio.

Day 2: Monday

For our first day of driving, we are heading east through the foothills on idyllic back roads. You will soon see that the Shenandoah Valley has some of the best scenery and roads in the world.

Our first stop will be at a private collection of antique and imported vehicles, followed by a delicious lunch at a winery & restaurant.

From here, we will continue to the delightful Wood Brothers Racing museum before making our way back to our host hotel..

For dinner, we’ll walk across the bridge to Billy’s Roanoke. This establishment resides in a building built in 1912 and offers a fabulous dinner experience.

Day 3: Tuesday

This morning we’ll head north on some really cool mountain roads to The Homestead Resort in Hot Springs, VA, a property that has operated as a hotel since 1766. We’ll take a tour of the grounds before heading back inside the resort for some food.

After a lovely lunch in the crystal ballroom, we’ll take a relaxing drive back to our hotel.

Dinner is on your own tonight, so you can eat at one of the two hotel restaurants or take a quick walk downtown where there are dozens of great choices.

Day 4: Wednesday

Today we will head southeast to VIR (Virginia International Raceway). This is one of our favorite tracks, and you’ll get a chance to see for yourself why we love it so.

We will have lunch on-property at the Oak Tree Tavern, a restored plantation home from the 1800s. After lunch we will head west on more fantastic, twisty roads back to the hotel. Dinner tonight is a surprise and will be a treat at one of Roanoke’s best and most famous restaurants.

Day 5: Thursday

Today we head north again to The Natural Bridge. This attraction has beguiled onlookers for as long as mankind has inhabited the area. After that, we’ll have a lunch with fantastic views at the Devil’s Backbone, then swing by another private collection before the day is done.

After our visit we will wind our way back down the Blue Ridge Parkway towards our hotel.
Upon our return, we’ll have drinks followed by our farewell dinner.

Day 6: Friday

We’ll enjoy breakfast at the hotel before checking out and parting ways (until next time).

 

Shenandoah Valley Tour Itinerary:

This is a tentative schedule - destinations and activities are subject to change

Day 1: Sunday

Relax, unwind and enjoy the amenities at the Hotel Roanoke or hop right into the historic downtown area, see the sights, and maybe even do some shopping in the market square. Whatever you choose, make sure you stop by the lobby to see us at the registration table to get what you’ll need for the week’s adventures.

After everyone has a chance to unpack and freshen up, we’ll head to our welcome cocktail reception and dinner on the hotel’s patio.

Day 2: Monday

For our first day of driving, we are heading east through the foothills on idyllic back roads. You will soon see that the Shenandoah Valley has some of the best scenery and roads in the world.

Our first stop will be at a private collection of antique and imported vehicles, followed by a delicious lunch at a winery & restaurant.

From here, we will continue to the delightful Wood Brothers Racing museum before making our way back to our host hotel..

For dinner, we’ll walk across the bridge to Billy’s Roanoke. This establishment resides in a building built in 1912 and offers a fabulous dinner experience.

Day 3: Tuesday

This morning we’ll head north on some really cool mountain roads to The Homestead Resort in Hot Springs, VA, a property that has operated as a hotel since 1766. We’ll take a tour of the grounds before heading back inside the resort for some food.

After a lovely lunch in the crystal ballroom, we’ll take a relaxing drive back to our hotel.

Dinner is on your own tonight, so you can eat at one of the two hotel restaurants or take a quick walk downtown where there are dozens of great choices.

Day 4: Wednesday

Today we will head southeast to VIR (Virginia International Raceway). This is one of our favorite tracks, and you’ll get a chance to see for yourself why we love it so.

We will have lunch on-property at the Oak Tree Tavern, a restored plantation home from the 1800s. After lunch we will head west on more fantastic, twisty roads back to the hotel. Dinner tonight is a surprise and will be a treat at one of Roanoke’s best and most famous restaurants.

Day 5: Thursday

Today we head north again to The Natural Bridge. This attraction has beguiled onlookers for as long as mankind has inhabited the area. After that, we’ll have a lunch with fantastic views at the Devil’s Backbone, then swing by another private collection before the day is done.

After our visit we will wind our way back down the Blue Ridge Parkway towards our hotel.
Upon our return, we’ll have drinks followed by our farewell dinner.

Day 6: Friday

We’ll enjoy breakfast at the hotel before checking out and parting ways (until next time).

 

Shenandoah Valley Tour: Before all spots fill up

Shenandoah Valley Tour

The Shenandoah Valley, nestled between the Blue Ridge and Ridge-and-Valley Appalachian Mountains,


By Colin Wood
Oct 3, 2025

The Shenandoah Valley, nestled between the Blue Ridge and Ridge-and-Valley Appalachian Mountains, boasts a kind of stunning natural beauty and destinations that can be found in few other places around the country.

That’s what inspired us to host our very first Shenandoah Valley Tour June 21-26, 2026.

Join us as we explore the unique history and scenery of the Shenandoah Valley while visiting exclusive collections and enjoying hand-picked dining experiences.