A Long Weekend Itinerary for Virginia's Shenandoah Valley

Day 1: Exploring Waynesboro

First on the agenda is a visit to charming downtown Waynesboro! Just 3 miles from the Blue Ridge Parkway sits this charming and scenic small town. Its historic Main Street is packed with small shops, museums and eateries to discover and even boasts a colorful collection of stunning murals that can be found on many of the buildings throughout town. 

Things to do & see in Waynesbor0:

Shop Local: There are quite a few locally owned shops and boutiques here in town to check out! Here were a few of my absolute favorite finds…

 

Pyramid – focused on all things Appalachian magic and remedies + incredibly cool and full of surprises

Shenandoah Valley Art Center– Packed with art work and goods created by local artisans

Stone Soup Books – Adorable locally owned book shop with so many fun finds

Learn the History: The Waynesboro Heritage Museum is situated in the heart of downtown Waynesboro and is the perfect spot to take in a little local history. The exhibits here are easy to move through and tell so many unique stories about the town’s historic past allowing you to take in as much or as little as you’d like depending on how much time you have! 

See the Murals: To get the full Waynesboro Street Arts Trail experience start by downloading the Street Arts Trail app! From there you will be lead through a fun scavenger hunt experience taking you around town to see all 20 spectacular murals. Even if you don’t have time to do the entire trail, I highly recommend checking out at least a few of these stops because they are absolutely stunning and something that is so unique to this colorful small town. 

Where to Dine & Drink in Historic Waynesboro:

The River Burger Bar: Situated right off of Main Street, The River Burger Bar is an outdoors inspired eatery featuring a full bar and a fantastic menu packed with lots of yummy apps (Think Wisconsin cheese curds, fried green tomatoes, and buffalo infused tater tots) in addition to their selection of burgers and sandwiches. The food here was SO good – highly recommend for lunch or dinner! 

Basic City Brewery: Basic City Brewery is known for it’s lively atmosphere and is always a fun time to visit! Featuring a great craft beer selection and food menu! 

After exploring Waynesboro’s Historic Main Street, hikers and outdoor adventure lovers will want to be sure to build in time to hit a very unique trail just a few minutes outside town. The Blue Ridge Tunnel Trail recently opened to allow hikers the chance to travel through a jaw-dropping train tunnel that was hand carved out of the mountain here in the 1800’s. When it first opened, in 1858, it was the longest tunnel in the United States and even among the longest in the world. Today it is considered by some to be one of the coolest hikes in America, and is certain to be a unique and exhilarating experience for all that travel through it. To begin the trail at the Waynesboro trail head head to 483 Three Notched Highway where you will find parking, click here for more details on the Blue Ridge Tunnel Trail and what you’ll need to bring along with you!

Check in to the Blackburn Inn ( book for 2 nights ):

Located just a short drive from Downtown Waynesboro is Historic Staunton, where you’ll find your boutique hotel stay for the first 2 nights of this getaway! Located just steps from downtown, the location makes for the perfect home base to explore from. Upon approaching the main drive leading to the Blackburn Inn you will be greeted by its stunning greek revival style architecture and towering white columns. The dramatic structure both outside and in, serving as a reminder to this buildings unique history as a psychiatric hospital in the 1800’s (not to worry, no signs of any ghosts during my stay).

Inside, elegant vaulted ceilings and archways framed by intricate molding define each light-filled hallway. The inn features 49 luxury guest suites with a variety of different layouts for every taste and budget. There is so much to see and experience here at the Blackburn Inn from the onsite dining at the Second Draft Bar and Bistro to the Inn’s art gallery and onsite spa. This summer, the Inn is even hosting its own live music concert series – click here to check out the calendar to catch a fantastic show under the stars during your stay. 

Day 2: Exploring Staunton

Considered by some to have one of the most beautiful Main Streets in America, Staunton is known for its blend of progressive culture and deep rooted history. Staunton truly has it all – from its one of a kind museums and historic architecture to its lively downtown packed with boutique shopping, eateries and even an iconic theater scene. There is a little something for everyone here so prepare for a busy day two! You can also check out a video feature on my day spent in Staunton by clicking here for the Instagram Reel

Things to do & see in Staunton:

Visit The Museums: If you are only going to visit one museum here in town I highly recommend making it the Frontier Culture Museum, a living history museum that tells the story of early American immigrants and the merging of their many cultures when creating the few frontier. Start your morning here so that you can spend as much time as you need exploring the grounds – there is SO much to take in! Other museums in Staunton that are worth visiting include the Woodrow Wilson Presidential Library and Museum and The Camera Heritage Museum. 

Shop Local: Take a stroll in historic downtown Staunton and shop from the 50+ locally owned boutique shops scattered around town. There are too many great shops here to name favorites so give yourself a good bit of time to explore here!

Live Theater: Catch a show at the American Shakespeare center’s iconic Blackfriars Playhouse – the world’s only re-creation of Shakespeare’s indoor stage. Click here to for their 2022 lineup to see what’s on stage during your visit! 

Where to Dine & Drink in Staunton:

Reunion Bakery: Perfect for a quick and delicious breakfast, Reunion Bakery is located just a quick walk from your hotel room at the Blackburn inn.

Remedy Burger: at lunch time head over to Remedy Burger for what will be one of the best cheeseburgers you will have in your entire life ( & don’t forget to order a side of truffle fries, you’ll thank me later).

Zynodoa: For dinner make a reservation at Zynodoa for a truly amazing farm-to-table dining experience right in the heart of downtown!

Day 3: Exploring Augusta County

Check out of the Blackburn Inn and hit the road for a day exploring and experiencing the beautiful scenery found in surrounding Augusta County. Today is all about the great outdoors and the magical experiences and sights found here in this corner of the Valley. 

Walk an Alpaca:

Start your morning off with a fun and unique hands on activity at Point of View Alpaca Farm located in Mount Sidney, Virginia. Not only does this beautiful farm allow visitors an opportunity to meet their friendly Alpaca residents but also take one for a scenic walk on property! This is an absolute must do and was a highlight of my Shenandoah Valley trip, to check out my video feature of the Walk-A-Paca tour click here for the Instagram Reel! 

This experience must be booked in advanced. For pricing and bookings click here. 

Explore Natural Chimneys Park:

Next stop is one of Virginia’s most underrated parks, Natural Chimneys Park located in Mt. Solon, Virginia. The star attraction here at this park – Seven rock formations that date back millions of years and tower over 120 feet tall. During my visit the park was hosting the Red Wing Roots music festival which I got to check out for a few hours and now am absolutely dying to come back for next year (highly recommend bookmarking this and checking it out in 2023)! If you aren’t as lucky to find yourself at the park during an event there is still plenty to take in and see with a few great hiking trails and plenty of awesome spots for a Summer picnic! 

Check in to Inn at MeadowCroft (1 night)

For your final night here in the Shenandoah Valley check in for a stay at the Inn at MeadowCroft in Swoope, VA. This charming bed and breakfast is housed in a beautifully renovated historic log home in Swoope, Virginia and is surrounded by stunning countryside. The Inn offers 6 lux guest suites to choose from (Highly recommend booking a room with a soaking tub!) and includes a scrumptious breakfast each morning. This stay truly is the perfect marriage between old and new —  with its luxury touches and sparkling clean spaces, it still maintains a simplistic countryside magic. 

A big thank you to Visit Waynesboro ,Visit Staunton ,and Visit Augusta County Virginia for generously hosting us during our visit. All recommendations and reviews remain genuine, these opinions are my own. 

Check out additional photos and video features about our weekend getaway in Virginia's Shenandoah Valley on Instagram & follow for more getaway inspiration

Subscribe To Stays & Getaways

Sign up & start receiving the monthly newsletter -