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Road Trippin’ – Cape Charles, VA

Sponsored By: AAA Car Care Center

Favorite Local Day Trips or Weekend Getaway?

Here’s one…. Cape Charles, Virginia.

Only about an hour’s drive from Hampton Roads, you will truly feel like you are “away” from the everyday world.  The drive over the Chesapeake Bay Bridge Tunnel is beautiful, as is the wide-open spaces along Route 13 as you drive north up the Eastern Shore.

A perfect day trip for me to Cape Charles involves a few “must have stops” along the way. Typically, I drive to the farthest stop north in the trip and make my way back towards home as the day progresses.

Stop One: Wine Time!

Chatham Vineyards

I start at Chatham Vineyards (it’s about 10 miles north on 13 past Cape Charles.

Jon and Millie’s story of how they started the vineyard and the story of their journey to becoming full time winery owners is so interesting.

They have wonderful outside seating and are excellent at following COVID prevention protocol.

You can pair your tastings with some lovely local cheeses and breads. My FAVORITE wine is the Charles Creek Vintner’s Blend (red).  Best Virginia Wine ever in my opinion and I always go home with a few extra bottles to enjoy at a later time.

If Wine isn’t your “thing” no worries; Cape Charles comes equipped with its very own brewery, Cape Charles Brewing.

A very cool set up with railroad cars as your backdrop in their outdoor seating area.  Great menu as well.  Spirits more your speed? No problem, you can also visit the Cape Charles Distillery!

Stop Two: A Late Lunch/Early Dinner

Option One:

The Oyster Farm at King’s Creek, they have a BEAUTIFUL VIEW. Their food is top notch and they have two awesome lifeguard chairs that provide a great photo opportunity. Our time there never disappoints.

Option Two:

My FAVORITE Virginia Pizza joint- Deadrise Pies.  Dining inside or out…. come hungry.  You won’t want to stop eating their delicious gourmet pizza creations!

Option Three:

Looking to eat on the water while in ? Then you will definitely want to visit the Shanty. Another incredible view.  My favorite item there is  SEARED TUNA NACHOS with wasabi drizzle. Yes, please!!

Where to spend your time in between libations and eating? Cape Charles has several options.  Here are a few of my favorites:


There are many antique places to stop at off of Route 13.  One we like is R & T Nautical P V C Bird.

Strolling Downtown

The downtown area of Cape Charles is adorable, with so many charming shops and eateries/ice cream, desserts…. We always come home with a little something to remember the outing by.

For great dining options, check out: capecharlesvirginiascape.com

Outdoor activity?

Get out on the water…. As a family, by yourself, or as a couple in a kayak at Southeast Expeditions.

Hiking and Camping

Hike a bit or stay a few nights. The following offer enjoyable camping and cabin options. Kiptopeke State Park


or KOA Cape Charles

Treat Yourself

Staying at the Hotel Cape Charles is a very special way to “get away” while staying close to home.

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Truly, a SoHo feel found right on the Eastern Shore. The beach is a short walk to the end of the street.

Another very satisfying overnight stay can be found in one of the towns many vacation rental homes and B & Bs. Click here for available accommodations:  capecharlesvirginiascape.com/category/accommodations

Rather you head up the Eastern Shore for the day, an overnight stay, a getaway weekend, or even longer, Cape Charles is a hidden little gem located very close to home.

You will definitely return refreshed and recharged and ready to take on everyday life again!


Like we always say, Safety First!  Before you hop in your car – make sure it is road ready.  Our friends at AAA Car Care Center are always ready to help you get safely on the road and off to your new adventure.

For More Road Trippin in the 757 check out the following:

Road Trippin in the 757 Heads to Currituck County

Road Trippin in the 757 Checks Out 6 Sits Commemorating African American History in Chesapeake

To watch this week’s entire episode of Living 757, click here!

And if you would like to see someone featured on the show, please send a message to Share@Living757.com and you may just see them here soon!