There’s something irresistible about Staunton, Virginia. It’s one of those towns that quietly surprises you – full of mountain views, cozy cafés, Shakespeare plays, and boutique shops that make you say, “Okay, I could actually live here.” That’s what happened to my cousin!

If you read my 10 Fun Things to Do in Staunton, VA, you already know this little Shenandoah Valley town packs plenty of charm.

Now let’s turn that list into an actual 48 hour itinerary – the perfect way to spend a weekend in Staunton, from Friday evening to Sunday brunch.

48 Hour Staunton itinerary

Day 1 – Friday: Arrive & Ease Into Small-Town Charm

Afternoon / Early Evening:

Arrive in Staunton, check into your hotel, and stretch your legs downtown. If you stay central, everything you need is within a few beautiful blocks.

Where to Stay

• The Blackburn Inn – Elegant, historic, and walkable. Think big windows, spa tubs, and quiet courtyards.
• Hotel 24 South – Budget-friendly and right on Beverley Street. Great hotel that we stay at.
• The Historic Inn at Oakdene – For boutique luxury and B&B warmth.

Drop your bags, then wander Beverley Street which is the heart of downtown Staunton – lined with indie boutiques and art galleries. If you arrive early, try Ox-Eye Vineyards Tasting Room downtown or Stable Craft Brewing just outside town.

Dinner Options

• The Depot Grille – Casual, lively, and built in a restored train station.
• Zynodoa – Upscale farm-to-table dining showcasing local Shenandoah Valley farms. Splurge night done right.

Evening:

Catch a performance at the American Shakespeare Center’s Blackfriars Playhouse. Even if you’re not a Shakespeare fan, the candlelight, audience interaction and energy make it unforgettable.

Tip: Let your server know you need to make the show so they get you in and out quicker.

Day 2 – Saturday: Explore, Eat and Enjoy the Outdoors

Morning:

Start with coffee and breakfast at The By & By Café or Réunion Bakery & Espresso (don’t skip the pastries!)

Then head to the Staunton Farmers’ Market held on Saturday mornings. Just make sure to check their hours as it can vary seasonally.

Afterwards visit the Frontier Culture Museum, an open-air museum where you can wander through historic homesteads, see costumed interpreters, and get a real sense of Virginia’s early settlers.

Give yourself 2-3 hours here as it’s bigger than you expect.

Afternoon:

Head back downtown for lunch at Cranberry’s Grocery & Eatery (healthy, veggie-friendly) or Remedy Burger for a more hearty meal.

Then choose your adventure:

1. History Buffs: Visit the Woodrow Wilson Presidential Library & Museum.
2. Shoppers: Dive into Staunton’s vintage and antique scene. Try the Staunton Antiques Center.
3. Nature Lovers: Take a short drive to Betsy Bell Wilderness Park for easy trails and sweeping views of the Shenandoah Valley.
4. Wine lovers: Drive to Hazy Mountain Vineyards then Barren Ridge Vineyards. There are others in the vicinity but these are 2 of my favorites within a short drive.

If you’re not into browsing museums, consider an outdoor adventure in the morning and a winery or two in the afternoon. There are also lots of spots to get cider in the area, but I’m saving those for my Harrisonburg article as the towns are so close.

Evening:

Ready for dinner? There are a couple additional restaurants to try:

• The Shack – Elevated local dining with creative small plates (reservations essential).
• Byers Street Bistro – Chill, fun, and great if you want a cocktail and comfort food.

After dinner, enjoy a relaxed walk through the Wharf Historic District, where old warehouses are now restaurants and art spaces. If it’s a warm night, you’ll probably hear live music drifting through open doors.

Day 3 – Sunday: Slow Morning & Head Home

Morning:

Sleep in a little, then enjoy brunch before heading out. Try The Pampered Palate Café for a tasty breakfast and coffee.

If you have more time, visit CoArt Gallery or Beverley Street Studio School Gallery for one last browse or make a quick detour to Skyline Drive for mountain views on your way home. You can pick up fixings for sandwiches to stretch out your day.

*Note there is a fee to drive Skyline Drive – see more info here.

Tips for Your Staunton Trip

• Best Seasons: Spring (blooms + mild temps) and fall (mountain foliage magic).
• How Long to Stay: Two nights is perfect for first-timers or combine with a longer trip to other nearby towns.
• Parking: Easy – downtown has free and paid lots.
• Walkability: Totally doable. Staunton is compact and charming on foot.

Optional Add-Ons

If you’ve got extra time or want to make it a long weekend:

• Virginia Scenic Railway – ride through Blue Ridge scenery with a meal onboard. They also have special wine tasting rail event.
• Humpback Rocks – short but steep hike with killer views.

Two days in Staunton goes by fast but it’s the good kind of fast. You’ll leave feeling like you’ve been away longer than you have, full of good food, mountain air, and that small-town contentment you can’t fake.

It’s an easy escape with a lot of heart and one I’d happily do again (preferably in the fall, with a apple cider donut from the market in hand).

Related Reads:

• 10 Things to Do in Staunton, Virginia (That You’ll Actually Love)
• Harrisonburg VA Travel Guide: 15 Local Favorites + JMU, Food & Shenandoah Valley Sips
• 10 Things to Do in Fredericksburg, VA: A Local Travel Guide
• Weekend Getaways Near Virginia Beach (Under 4 Hours Drive)
• Virginia Bucket List: 20+ Must Visit Sites in VA