So you’ve finally made it to a long weekend (whether it be through a holiday or not). You want to maximize your time in the Shenandoah Valley without stressing yourself out. Welcome.

Stephanie and I finally got to experience a few long weekends since moving near Charlottesville, Virginia. And because Stephanie loves to plan, we’ve tested a few itineraries perfect for a summer or early fall visit. Let me share our ideas for an action-packed, yet relaxing, getaway.

First Night

When you first arrive, you may want to get out for a drink and dinner. Staunton is such a fun town. You can walk around shopping, dining, and exploring. We love swinging into The Well Balanced Paw in Staunton to pick up some treats.

From there, walk over to a quiet, cozy restaurant called Table 44. They have a full menu for pets, but their human food is amazing as well. Afterward, drive over to Barren Ridge Vineyards to watch the sun go down and sample their wines. Most nights, they stay open until 8 pm!

Day One

Once the Indigo is open, you’re invited to enjoy breakfast in bed, on the patio, in our dining room, or on the go if you are driving to your morning destination. Once you’re out and about, you can hit up one of the local trails (all dog-friendly) or pop over to the farmer’s market located at the golf course about 3 miles away (Saturday mornings only).

When the tasting rooms open (wine, beer, or cider), we’ll steer you towards one of them for lunch and an afternoon of music and fun. Our favorite dog-friendly spot to beat the heat is Bold Rock Cidery, as they have a cold creek to splash in, but there are numerous options to choose from.

Second Night

Some ideas for you to consider:

  • Grab takeout from the side-of-the-road BBQ at Paulie’s Pigout or Blue Ridge Pig and spend the evening with us. We can throw up a hammock, get a fire going, and trade life stories.
  • Make reservations at the Farmhouse at Veritas for a four-course dinner. Seatings are limited and meals are wine-paired featuring homegrown and house-made Farm-to-Fork menus.
  • If you are having snacks at every vineyard or grabbing nachos at Brewing Tree, then you might not be hungry for dinner. Instead of going out, you can read a book near our fireplace, take a bath, or watch the sunset from the Indigo. We plan to have snacks available, in case you get peckish.
  • Wood Ridge Farm Brewery has good food and a hemp maze you can get lost in.
  • Blue Mountain Brewery always has the game on or live music. They are open later than most of the vineyards around, so you can make a whole evening out of visiting them.

Day Two

Wake up slowly and grab a picnic basket to take for tailgating at Roseland Polo at King Family Vineyard. You’ll want to get there right when they open at 10 am to grab a good spot. Don’t worry about packing drinks, as they have a cart that delivers their bottles right to your spot. Watch the matches (at 12 and 2 every Sunday) until you’re ready to explore the charming town of Crozet.

If you haven’t had lunch, grab food from Greenwood Grocery or Pro Re Nata Brewery. Stop in the local country store for gifts. Hike some of the trails you missed before, check out some more tasting rooms, or drive Skyline drive to see some amazing overlooks from Shenandoah National Park. We always recommend an afternoon of winging it!

Last Night

When the sun starts setting on your last night, we recommend driving Blue Ridge Parkway or Skyline and taking in a sunset hike. Some of our favorite trails:

  • Humpback Rocks- This free trail is tough but short.
  • Turk Mountain Overlook- Inside Shenandoah NP, this is an easy mile to the overlook.
  • Blackrock Summit- lots of bang for your buck! It’s more driving than hiking but the views are worth it.

Of course, you can park at the overlooks and watch the sun go down without breaking a sweat.

Day Three

Although we hate to see you go, life doesn’t stop. Unfortunately, you’ll probably have to get home to get back to work, take care of the kids, and do your laundry. We hope you picked up a few bottles as souvenirs to bring a little bit of your vacation home with you.

Look forward to seeing you for a three-day weekend soon!