Cape Charles, Virginia

Long-suffering man and his pup

As the default “cruise director” for day trips with my girlfriends I’m comfortable with the planning process for ensuring a fun time on the road. Pick a spot no more than a couple of hours drive from Richmond, collect the names and addresses of several coffee shops, diners and art galleries and make sure they’re open when you plan to visit and be sure to invite friends who enjoy discovering unexpected delights.


The last “must have” is critical; flexible friends who easily revert to a “Sounds good to me” attitude when plans change are a key ingredient to a carefree, interesting day trip. Too noisy at lunch choice #1? Let’s try the second cafe on our list, or the new deli we discovered when we walked along Main Street. Didn’t know about this arts and crafts gallery; let’s peruse it before we have coffee. We’re super lost on these backroads but look at the painted barn quilt over there! The little rush of adrenaline you feel when a disappointment turns into a lovely surprise sticks with you and your fellow travelers for years and becomes part of your honey-sweet glue of friendship.


When I mentioned to my daughter that I had read about a long boardwalk/pier along the Chesapeake Bay in the town of Cape Charles, Virginia, she lit up. Unbeknownst to me she had been following her favorite bloggers’ posts about their renovation of two homes in the town and she was curious to see the area. That’s how it started, with a plan to walk the boardwalk and find the two houses she had been reading about for months. By the time we got in the car we had collected a few more places to see: an ice cream shop, a fine arts/crafts gallery, a restaurant at a marina (guaranteed water view for lunch) a large park in the town and a craft brewery. All set.

This day trip was very different than my usual because it involved family instead of girlfriends. Also, there were two men accompanying us—and three dogs. My SIL is easy-going and enjoys traveling. My long-suffering husband drives and goes where he is told; between my daughter and me he receives plenty of instructions. The dogs served as conversation openers with shop owners and other travelers but they did require lots of shade and water breaks on this mild summer day. I must remember to always scope out the temperature forecast when planning a canine-included trip.

It turned out to be a fairly relaxed and very enjoyable day. Some lessons I learned: consider the personalities and interests of each person in your group and choose at least one place that might be a treat for them. Our first stop of the day was a seafood eatery at the marina and this was a real pleasure for my long-suffering husband. It set the day out on a happy, gastronomical note.

After lunch we plunged into the hot, sweaty activity—walking the boardwalk. It was cooler than usual for summer in Virginia (mid-80’s) and the breeze from the Bay made it extra nice. But, it was definitely in the full sun and the dogs needed several water breaks. It was also the spot where the most folks stopped us and asked to pet the hounds, which added to their time in the heat.

Main street in Cape Charles is Mason Avenue. The shops begin just a block or so from the boardwalk and much of the street is shady, with well-placed benches for sitting and enjoying your Brown Dog Ice Cream or coffee from a nearby shop. There are also stores on the side streets between Mason Avenue and Randolph Avenue, so keep your eyes open for their signs. We found that the breeziest spot was in the shade along Strawberry Avenue. One of the shop owners along that street told us that it was the coldest place in town when the winter winds blew in. I was sad to learn that I had missed the sea glass art class that very morning at Lemon Tree Gallery but it was the kind of place I’d want to visit again to see the changing collections.

The long-suffering man greatly enjoyed the olde time hardware store and his ice cream but insisted he monitor the dogs while the rest of us explored the rest of the shops. Since Mason Avenue offers about six blocks of shops that left us enough time to explore the nearby homes with their storybook yards. Peach Street was our main target, since we hoped to find the renovated homes my daughter was interested in locating. Sure enough, we saw them both and even caught a glimpse of one of the blog authors as they toiled away outdoors. Mission accomplished!

If you have kids with you be sure to have a ball and glove in your backpack because Central Park is the perfect place to play catch. My daughter and SIL took the dogs to the huge pavilion to cool off in the shade and I scoped out the fountain. The park is as large as a college green and surrounded by well-maintained homes with large porches, with many painted homes in pastel colors. The hydrangeas were out in force, slathering the corners of homes with blues and pinks.


My born-to-serve husband walked back to town to retrieve our car, collected us and we headed out to our last stop—Cape Charles Brewing Company. Sure enough, there was a shady picnic table waiting for us and the dogs filled up on water and headed over to the railroad tracks for a pit stop while the guys went in to order. I was surprised to look down the abandoned RR tracks to see a vehicle coming toward us. Not a train but one of the many golf carts we had seen cruising through town. The owner of the Brewery later told us that they had petitioned the town council to allow a pathway parallel to the tracks for the carts, so customers could safely drive on a shortcut from town to the business. Yes, it was great. I recommend the “Puddle Pirate Porter.”

The trip back to RVA was much shorter than the morning drive but that toll on the Chesapeake Bay Bridge Tunnel was just as steep on the return leg—$18. No matter--with three hounds and four humans we got our money’s worth.


What worked to make this day trip a winner? We had some options in hand for places to see and were open to changing plans if better opportunities showed up. Half to three-quarters of the humans generally have positive attitudes and the rest of the travelers put effort into being cooperative and helpful. We all shared in taking care of the hounds—walking them, watering them, finding shade for them, picking up “stuff," hoisting them in and out of the car. The day wasn’t just about “us” but also about the four-legged “them.” I kind of had the feeling that all of us were on our best behavior with one another and had left the “Complaining” button at home. Treating each other like friends. A good thing, eh?

There are many places to try in Cape Charles that we didn’t have time to enjoy.  Explore and tell me what you find!

We visited:

Oyster Farm Seafood Eatery

Cape Charles Boardwalk

Brown Dog Ice Cream

Lemon Grass Gallery

Watson's Hardware

Central Park

YoungHouseLove home(s)   YHL Homes

Cape Charles Brewing Company


*Thx to my camera-savvy SIL for the puppy photo pics!