Shenandoah National Park is nestled in the Blue Ridge Mountains of Virginia. The park itself is long and narrow while the surrounding area is full of small towns. I enjoyed the views at the park and the various trails, but wouldn’t want to spend too much time in the nearby towns.

Planning a road trip? Check out my guide to nearby Washington D.C. here, Baltimore here, and Richmond here!

Shenandoah National Park Recommendations:

Shenandoah National Park is relatively small and mostly based around one main road: Skyline Drive. You can easily tackle a good chunk of this park in a couple of days! I would recommend trying to visit on weekdays instead of weekends as much as possible just because it is quite popular and there are many large cities within quick driving distance that people visit from. You will need a National Park Pass or to pay to enter the park. One note—at this park most of the trailheads do not have bathrooms so keep that in mind when starting your adventures!

Mary’s Rock via Appalachian Trail: This trail is 4.4 miles long with 1,210ft of elevation gain and takes about 2 hours to complete. The trailhead is just after the park entrance so there is ample parking here and a bathroom. It is a steep, steady and rocky climb up, and this trail is rated hard. It leads to a beautiful viewpoint of the surrounding area. Dogs are allowed on this trail!
Berry Hollow to Old Rag Mountain Trail: This trail is 6.5 miles long with 1,751ft of elevation gain and takes about 2.5 hours to complete. Permits are required to hike Old Rag, so be sure to snag one before heading out. It is rated hard. Heads up this is one of the only trails in the park that is not off the main road, Skyline Drive. Parking is quite limited so try to arrive early. The traditional route for Old Rag is much more popular and more difficult at 9.3 miles long with 2595ft of elevation gain and many scrambles. Choose your own adventure!
Stony Man via Appalachian Trail: This trail is 1.5 miles long with 321ft of elevation gain and takes about 35 minutes to complete. It takes you through the woods to a pop out with a nice view of the surrounding area. It is rated moderate but was a pretty quick, steady climb up.
Dark Hollow Falls Trail: This trail is 2.1 miles long with 583ft of elevation gain and takes about 1 hour. It is a popular trail but not overcrowded and leads to a nice waterfall. There is also one more viewpoint at the bottom on a wooden bridge. It is a relatively steep climb back up to the parking area, and this trail is rated moderate.
Hawksbill Summit Trail: This trail is 1.9 miles long with 672ft of elevation gain and takes about 50 minutes to complete. It is the highest peak in the park and a short trail so it is quite popular. It is a very steep hike up but since it is so short it is rated moderate. Dogs are allowed on this trail! An alternative option is the Hawksbill Loop Trail which is just a bit longer and takes you around the summit instead of straight back down.
Take the scenic drive down Skyline Drive: There are overlooks throughout the straight shot drive from one end to the other. Boldface Mountain is a nice overlook on the south end of the park. If you have driven the Blue Ridge Parkway this has very similar vibes.
Bearfence Mountain Trail: This trail is 1.4 miles long with 242ft of elevation gain and takes about 40 minutes to complete. This trail is full of rock scrambles so it is definitely not for kids or folks afraid of heights. Keep your eyes peeled for rattlesnakes as well. It is rated moderate. I did not love this trail because there was not a view at the actual summit, just some views with the rock scrambles along the way.

Shenandoah Valley Recommendations:

Broad Porch Coffee: A fantastic spot in downtown Luray for breakfast and coffee. They have a cute spot with indoor seating and a back porch with river views. I went two days in a row because I enjoyed it so much!
Elkton Brewing Company: A solid brewery in Elkton with a nice outdoor space. They have food trucks on the weekend, they are dog friendly and they are housed in a nice historic building.
Quièvremont Vineyard & Winery: A nice winery with great views in Washington, VA. They also have food options. Heads up it gets quiet popular on weekends!
Vibrissa Beer: Vibrissa has two locations in Front Royal and Winchester. They both have full food menus and outdoor seating as well.
Gathering Grounds: A solid spot for breakfast in downtown Luray.
I stayed at this Airbnb which was nice, but I would probably stay somewhere with a better view if I visited the area again. The outdoor space and screened-in porch were lovely.
Wisteria Farm and Vineyard: An average winery in Stanley. The wine is fine but there are no views and the food is very overpriced and prepackaged. They are dog-friendly and you can bring your own food as well. It is a very casual spot and people loved it, I just wanted a bit more out of it.
Pen Druid Brewing: A brewery with nice views in Sperryville. It was not my personal favorite but it’s worth checking out. They have an onsite food truck, Sumac.

Harrisonburg

Jack Brown’s Beer and Burger Joint: A simple spot for burgers and drinks in downtown with absolutely delicious eats. Highly recommend!
Brothers Craft Brewing: A nice brewery just outside of downtown Harrisonburg. They have indoor and outdoor seating with chill vibes.
Restless Moons Brewing: An average brewery with interesting vibes. I definitely watched multiple drug deals happen here. Their tap list is Sour heavy and they have pinball machines for entertainment.

The Delmarva Peninsula is home to portions of Maryland and Delaware with nice beaches and some great breweries. This guide goes sequentially driving south to north from Berlin Maryland to Cambridge Maryland after adventuring along the coast.

Berlin, Maryland

Burley Oak Brewing Company: This hype brewery is Sour focused but also makes tasty IPAs. They have a large outdoor space with frequent events. They do not have any food and they do not allow dogs inside or out. Located 15 minutes from Ocean City.

OCean City, Maryland

The Other One Brewing Company: A solid brewery with a small food menu and non-beer options. They have a dog-friendly shared patio space and are on the south end of Ocean City.
Stay at the Home2Suites Ocean City Bayside: This is a nice hotel in a good location and is reasonably priced for the area.
Grab ice cream at King Kone, it’s fantastic!
Check out Northside Park—this is a great spot to walk, run, or take your dog.

Dewey Beach, Delaware

Dewey Beer Company: Dewey has two locations—the original space is a block from the beach in Dewey Beach and their new space in Harbeson, about 30 minutes inland. The beach location has a ridiculously delicious food menu and Harbeson has their newest venture Pizza Machine next door for ‘za. Parking at the beach location can be a little challenging, while Harbeson has ample spots. Sours are what Dewey does best but their IPAs are also good. Dogs are allowed on the patio at the beach and inside and outside at Harbeson.

Rehoboth Beach, Delaware

Dogfish Head Brewery has multiple locations—Brewing & Eats is their restaurant and taproom in Rehoboth, emPOURium is next door with cans, and Chesapeake and Maine is the next building with seafood and cocktails. Dogfish Head’s main brewing facility and tasting room is in Milton, DE.
Stay at Home2Suites Rehoboth: A nice, updated hotel with tasty breakfast and great amenities.
Thompson Island Brewing Company: A restaurant-style brewery with average beers. It is a beautiful space with a small outdoor space in both the front and back. The space is beautiful, but the location is a bit odd next to a gas station. No dogs allowed.

Lewes, Delaware

Wander downtown: This is an adorable small town full of shops, restaurants, and parks.
Olive and Oats: A cute spot for coffee, breakfast or lunch in the heart of downtown.
Dogfish Head Brewery has an Inn to stay at right downtown!
Big Oyster Brewery: The beers here are solid but the vibes are not great. They have a full food menu and operate in the style of a restaurant. Half of the seating is in an outdoor tent with plastic dollar store chairs. Skip the pretzel, eat the oysters.
Grab the ferry to Cape May, New Jersey to extend your adventures. Reservations required.

Wave goodbye to the beach, it’s now time to head inland—

Delmar, Delaware

Loakal Branch Brewing Company: This is a subsidiary of Burley Oak Brewing and more of a local’s dive bar than anything else. I found this to be a very odd spot and not worth visiting.

Salisbury, Maryland

Burnish Beer Company: A restaurant-style brewery with a full food menu and a large outdoor space. The food here is tasty and the beers are average. Dogs are allowed outside.

Cambridge, Maryland

RaR Brewing: A Sour focused brewery in downtown Cambridge. Their taproom, their Chessie Burger restaurant, and their cocktail bar The LaboRaRtory are all in a shared row. They have a ton of guest taps and guest cans in the taproom alongside a large house-made beer selection. RaR has a cool space with artwork and chill vibes, but the beers were a bit disappointing. There is no dog-friendly space here.

Shenandoah National Park Guide