Cape Charles, Virginia Day Trip Guide

Happy Tuesday! Over this past holiday weekend, Jarrett and I explored the nearby town of Cape Charles. This seaside escape is on the Eastern Shore of Virginia and just an hour from Virginia Beach. Knowing that we will not live in the Mid-Atlantic region forever, we are making it a priority to explore nearby cities in the next couple years. Cape Charles was an easy drive across the Chesapeake Bay Bridge and we had a blast exploring!

Tell me what you did over Labor Day Weekend! Or, have you been to Cape Charles before? Anywhere else on the Eastern Shore we should visit?

Interested in other travel guides? Check out Richmond (last year and this summer), Raleigh, or Roanoke.

Cape Charles, Virginia

Chatham Vineyards, Machipongo

We started off our afternoon at Chatham Vineyards, which is located approximately 15 minutes north of Cape Charles, in Machipongo. When I was researching Cape Charles, this little vineyard kept popping up! While we are usually focused on exploring breweries when we travel, Jarrett and I are trying to expand our horizons (and our palates), so we made this our first stop.

Chatham Vineyards offers a tasting, which includes a brief history of the property. It turns out that the land is some of the oldest continually farmed land in the country, dating back to the 1600s! The six-part tasting included three whites and three reds. I, personally, really do not enjoy white wine. However, Jarrett thought they were all good, particularly the oak-aged chardonnay. All of the red wines were good, but the vintner blend was my favorite.

We decided to each enjoy a full pour, along with a fresh bread and cheese platter. We also learned that they allow you to bring your own food to enjoy along with their wine! I would highly recommend bringing your own picnic if you are coming on a cooler day and plan to spend a few hours enjoying the beautiful scenery. Also, just a warning- there were tons of flies! They didn’t bite, but they definitely wanted our food.

Cape Charles Brewing Company

Next stop was Cape Charles Brewing Company. We find a brewery every city/town we visit, so this was a must-visit for us! The brewery offered a number of craft beers and a lunch/dinner menu. Jarrett and I split a four-beer flight, which included multiple IPAs, a hefeweizen, and a stout. The beer was decent, but compared to what is offered in Hampton Roads, not the best.

We both gave it a 6.5/10 overall. If you are passing through the area, I would suggest stopping in and giving it a taste though! Everyone was very friendly and service was great. We’re just beer snobs. Ha!

Brown Dog Ice Cream

This ice cream was by far the highlight of Cape Charles for me! I LOVE dessert, which you may or may not have gathered from the title of this blog. Now, there were not any speciality donut shops, but ice cream still works for me. And this ice cream was incredible! There is a reason it has been named in the top 10 ice cream shops in the country.

Flavors change daily and are updated frequently on the shops facebook page. The shop is seasonal, closing Labor Day Weekend, but can be found in many local restaurants year-round. I had saffron chamomile honey and it was incredible! The ice cream could not have been creamier and had the most consistent flavor. Jarrett had barely there malted milk ball and also enjoyed it! The lines are long, but well worth the wait.

The Shanty

Prior to dinner, we wandered through the small town a bit and walked down to the fishing pier. Cape Charles is very accessible, with many people in bikes or in golf carts, which appeared to be the preferred mode of transportation. There are a number of gift shops, a candy store, and a Buskey Cider location, if you are looking for other things to do! There is also a public beach and lots of public parking.

Alright, on to dinner. Neither Jarrett nor I were particularly hungry, but we couldn’t pass up local seafood at The Shanty. I had seen a number of great reviews and was excited to try it out! Luckily, we put our names in with the hostess around 5:30 and only had a 30 minute wait. People arriving after us were told over an hour, so clearly it was the dinner spot of choice!

I ordered the fried shrimp basket, which was delicious! Jarrett is not a huge seafood lover, so he opted for the Philly cheesesteak sandwich with fries. We were both too full from ice cream to finish our meals, but I would definitely return if we visit again.

The one negative about the restaurant was that it was hot! No air conditioning on a 100 degree day was tough. Otherwise, I would recommend!

We made the relatively quick drive home after that, settled into pajamas, and watched a movie. Not a bad way to spend the day!


Hope you all enjoyed this post! I will be heading to Charleston, South Carolina in a couple weeks, so look for a weekend guide soon 🙂

Questions? Comments? Words of Advice?

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