Travel Guide: A Weekend in Woodstock, VA and Shenandoah County

We spent a weekend in Woodstock, VA in Shenandoah County this fall and had the most perfect autumnal time. Shenandoah County was not a place familiar to me — I know of the Shenandoah region and a town called Shenandoah, but I didn’t realize that it was an entire county on the other side of the mountain from Luray. 

Shenandoah County is nestled in the Shenandoah Valley, right in between the Blue Ridge Mountains and the Alleghany Mountains. The towns include Mount Jackson, Strasburg, New Market, Edinburg, Toms Brook, and Basye, but we spent most of our time in Woodstock, the largest town in the county.

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Travel Guide: A Weekend in Woodstock, VA and Shenandoah County

How to Get to There from DC and Get Around: Weekend in Woodstock and Shenandoah County

Shenandoah County is an easy 2-hour drive out 66 from DC. We braved it at the worst time…right after work on a Friday. And it still wasn’t that bad.

Where to Stay for a Weekend in Woodstock and Shenandoah County

We stayed in a delightful Airbnb called The Valley Hideaway, owned by a woman who lives not too far away. It is the ground level apartment of a home and it’s completely separate from the upstairs unit. There are residents upstairs, but we never saw them. Also, ground level can have connotations of dark or basement-level, but this truly is light and bright. This two bedroom + office unit was one of the cleanest Airbnbs I’ve ever stayed in, and the kitchen and bathrooms were fully stocked. There is also a fire pit outside, solely for the use of Airbnb guests. It is a comfortable and affordable place to stay, and I’d imagine it’s even better if you’re traveling with a group or a child or two and need to prioritize comfort and space over a boutique hotel stay.

When to Go for a Fall Weekend in Woodstock and Shenandoah County

We went in mid-October and it was absolutely perfect fall weather. We lucked out with a mild to cool weekend, lots of sun, and vibrant fall foliage.

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Friday Evening in Woodstock

Dinner at Woodstock Cafe

As I mentioned, we left DC on a Friday after work, so we were pushing the limits of arriving to our dinner reservation by 8 PM. Thankfully, the staff at Woodstock Cafe was incredibly kind and, as our ETA pushed later, they took our order ahead of time so it could be ready when we arrived.

The owners of Woodstock Cafe, Nikki and Jose, opened the restaurant after working in hospitality everywhere from San Francisco to Chicago to DC, and they’re bringing gourmet takes on classic dishes to this homey cafe. We sat in a cozy booth, amidst a group that felt like regulars, and Nikki came over to chat, with her warm, welcoming demeanor shining through. We had the Parker House rolls, the Ribeye, and the Slow Roasted Heritage Pork, and each was mouth wateringly good. I’d literally order all three again. And the pave potatoes, a side with the Ribeye were a highlight, which consist of the most delicately sliced layers of potato, with crispy edges and a tender middle. They’re salty and buttery — the result of a multi day preparation process — and I’m still thinking about them and how I can try to recreate them at home (spoiler: I can’t).

Woodstock Cafe also serves breakfast, brunch, and lunch, and has a darling shop component in the back of the restaurant, with fun gift items (I wish I’d gone back the next day to browse — next time!), as well as a wine shop with specially selected wines from around the world.

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weekend in woodstock virginia - weekend in shenandoah county - woodstock cafe virginia

Saturday Morning in Woodstock

Pick Up a Pastry at Flour & Water Co.

We didn’t initially plan to stop by Flour & Water Co., but when I spotted it as we were driving to breakfast, I knew I wanted to pop in. They aren’t open on Sundays so, alas, I was in for a double breakfast Saturday morning.

It’s the most precious bakery, with bread, croissants, sconces, and more. I opted for the cardamom morning bun (though I declined the mimosa deal they had that morning — for a different kind of day, perhaps!). It was sticky, sweet, and delicious. I wish we’d had the foresight to grab bread and a few extra pastries to go.

weekend in woodstock virginia - weekend in shenandoah county - flour and water co

Brunch and Browsing at Woodstock Garden Cafe

As a perpetually aspiring gardener, I love a trip to the nursery, and Woodstock Garden Cafe lives within the gorgeous Woodstock Gardens. There are plants both indoors and out, of all varieties, as well as a charming shop with home and garden goods. I grabbed a latte and Adam opted for a coffee — both from local-ish Aperture Coffee, and we ordered breakfast. The Chipotle Cheddar Breakfast Sandwich is a can’t miss dish.

Note that Woodstock Garden Cafe is closed Sundays, too, so plan accordingly!

weekend in woodstock virginia - weekend in shenandoah county - woodstock garden cafe

weekend in woodstock virginia - weekend in shenandoah county - woodstock garden cafe

weekend in woodstock virginia - weekend in shenandoah county - woodstock garden cafe

Saturday Midday in Woodstock

Stroll Through Town and Do Some Shopping

Woodstock is a small, but charming town with shops of all types. I didn’t initially plan to do any shopping and thought I’d have more of an outdoorsy weekend, but we were there and the storefronts looked cute…

  • The Buttercup: This boutique carries clothing and accessories at all price points, and I picked up a leather crossbody bag that I’ve carried almost every day since. It’s from local Shenandoah Valley leather maker Alexander Brothers, which makes it so much more special (this is why I always try to buy from local makers rather than a department store!).
  • Nate & Main: The purveyors of this shop must have impeccable taste because it is the most beautiful collection of both new and antique goods. Their Instagram does not do them justice — it’s a refined, masculine aesthetic with a touch of grandparents’ house.
  • Spring Hollow Antiques: If you love old, old antiques, this is your spot. Everything felt perfectly suited for an early 1800s colonial, with wood and quilts taking center stage.
  • VECCA: I had to include VECCA because they have a fun art gallery with all local artists, and they showed us their back room where they are currently assembling the next in a series of mosaics like the one below. Such a cool process led by volunteers!

There are also several shops that we didn’t have a chance to pop in, but looked to have home goods, local items, and more. If there had been more time, I would have stopped in each and every one!

weekend in woodstock virginia - weekend in shenandoah county

weekend in woodstock virginia - weekend in shenandoah county

weekend in woodstock virginia - weekend in shenandoah county

Saturday Afternoon in Shenandoah County

Do a Wine Tasting at Muse Vineyards

We had the most delightful time at Muse Vineyards, a vineyard that sits immediately next to the Shenandoah River, with a tasting room and outdoor space that overlooks breathtaking views of the mountains. Owner Sally is a fascinating person with a story that includes serving as a U.S. Ambassador, and she told us how she and her husband first bought the property with the intention of making it a weekend home, but one grape vine turned into 35 acres — and here they are.

So here’s a secret about Virginia wine…and probably wine throughout burgeoning wine regions. Many of the wineries are blending grapes that aren’t actually grown on their property, or they’re at least supplementing. But not Muse. They’re invested in the science of the process and leaning into the rocky red clay soil. The result is wines that echo some of the best wines you’ve had from Italy, France, and elsewhere. I surprised myself by enjoying the Rosé the most (and I wish I’d grabbed more bottles than the one I bought on the way out!).

You can do a tasting with someone to guide you, or you can take your tastings outside in one of their innovative tasting holders. We chose to take ours outside and enjoy the gorgeous autumn day. The people watching out there was delightful, with so many groups of people of all ages — twentysomethings out for a big weekend, families with babies, and multi-generation groups — enjoying each other’s company and the fresh air of the Virginia countryside. We didn’t get any food, but they do have a kitchen, and several options to balance out your wine drinking. 

Muse Vineyards also has a farmhouse on property — it’s where the owners originally lived when they bought what is now the vineyard. It’s available to rent (and it has a pool for summer months!). You can’t beat walking to the tasting room, right?

weekend in woodstock virginia - weekend in shenandoah county - muse vineyards

weekend in woodstock virginia - weekend in shenandoah county - muse vineyards

Make a Pitstop at Filibuster Distillery

We hadn’t originally planned a stop by Filibuster Distillery but the signs tempted us as we drove by. The moody tasting room feels like the type of place I’d like to visit on a cold, blustery day, though there’s also outdoor seating for sunny weather.

We did a tasting and, since we were driving, we weren’t able to indulge in the cocktails, but don’t worry, you can also purchase bottles of bourbon for when you don’t have anywhere to be but home.

weekend in woodstock virginia - weekend in shenandoah county - filibuster distillery

weekend in woodstock virginia - weekend in shenandoah county - filibuster distillery

Saturday Late Afternoon in Strasburg

Search for Vintage Treasures

We did a quick stop in Strasburg because I’d heard the Strasburg Emporium was worth a stop. I didn’t find anything I needed but this is a massive market that could take hours to peruse. It has a mix of country-inspired items as well as classic finds and, with enough digging, you’ll certainly find treasure.

We also popped in Clementine Vintage, which I loved. This darling shop has so many cool, eclectic finds. There was art, a picnic basket, furniture…I could have gone home with so much. But I practiced moderation and only left with a pair of old fashioned glasses

Saturday Evening in Edinburg, VA

Get a Pizza and Beer at Swover Creek Farms

After a busy afternoon, we ran back by the Airbnb to put on some warmer clothes before heading out to Swover Creek Farms & Brewery. This serene spot in the woods is somewhere you won’t get much cell service, which I can appreciate on a weekend when I’m trying to unplug. There was live music, indoor and outdoor seating, and the best kind of Saturday night food, pizza and beer.

We spent several hours sitting under the twinkle lights, listening to a duo play folk music while eating a delicious wood fired pizza and drinking craft beer. You can’t beat this for a fall evening.

weekend in woodstock virginia - weekend in shenandoah county - swover creek farms

Sunday Morning

Go for a Hike in the Mountains

I’ll be honest…we didn’t do this. I was on week three of getting over a terrible cold, and I just couldn’t. But, if you were to hike, here’s a list of several of the hikes in the area you could do. Based on how incredible the views are, I can only imagine a walk up the mountains gets you an even better viewpoint.

weekend in woodstock virginia - weekend in shenandoah county virginia

Grab a Beer and Lunch at Woodstock Brewhouse

Before we headed back to DC, we made one final stop at Woodstock Brewhouse, a place that had come highly recommended by friends who’ve been to the area. It’s great casual bar food, exactly what you’d expect, and the wings hit the spot.

Personally, I was excited to see several dark beers on the menu. Too few breweries offer more than one dark selection, and there’s nothing I want more than a porter or a stout once there’s a chill in the air. Woodstock Brewhouse came through — and I tried both since Adam and I shared a tasting. The Pumpkin Ale was another surprise favorite for both of us.

weekend in woodstock virginia - weekend in shenandoah county virginia - woodstock brew house

Head Home with Fall Memories in Tow!

With that, our weekend in Woodstock and Shenandoah County came to an end, and we headed back to DC, scheming about the next time we can get back out to the mountains.

weekend in woodstock virginia - weekend in shenandoah county virginia - hanging bridge woodstock virginia

Recommendations by Category | A Weekend in Woodstock and Shenandoah County

Where to Eat and Drink in Woodstock and Shenandoah County

Woodstock Cafe

Woodstock Garden Cafe

Flour & Water Co.

Where to Shop in Woodstock and Shenandoah County

The Buttercup

Nate & Main

Spring Hollow Antiques

Strasburg Antique Market

Clementine Vintage

Vineyards, Breweries, and Distilleries to Visit in Woodstock and Shenandoah County

Muse Vineyards

Filibuster Distillery

Swover Creek Farms & Brewery

Woodstock Brewhouse


Thank you to Visit Shenandoah County for inviting me out to experience your beautiful home and spend a weekend in Woodstock and throughout Shenandoah County. My lodging was covered, as was a small stipend towards expenses. As always, all opinions are my own!


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