Annapolis and Alexandria’s Del Ray are two of the area’s most dog-friendly spots. In Annapolis, you can start at Quiet Waters Park, which has six miles of paved trails, two dog parks, and a dog beach where you’ll find pups chasing toys along the sand while others splash in the South River. Later, you can bring your dog into town: Many Annapolis restaurants, including Harry Browne’s and Purple Tooth Wine Bar, welcome pets in their outdoor areas.

If you visit on a Friday this summer, you might catch one of the monthly Canine & Cocktails for a Cause events at the pet-friendly Loews Annapolis Hotel. Visit Paws Pet Boutique’s Web site (pawspetboutique.com/news_events.shtml) for a schedule of events, which benefit organizations such as the SPCA. If you’re heading to Annapolis for the Fourth of July, both you and your pup are welcome to march in the parade. There will be a dog pool halfway through the route.

In Del Ray, start your morning at St. Elmo’s Coffee Pub with a cup of joe for you and a dog treat for your furry friend. Make your way to Barkley Square, a dog bakery that hosts workshops on reiki and massage therapy for dogs and offers an outdoor patio with wi-fi Internet, water bowls, and benches where dogs and their owners can lounge. Pick from any of Del Ray’s restaurants for lunch or dinner—almost all will let you dine outside with your dog. You might want to end the day on a sweet note at the Dairy Godmother: In addition to the Wisconsin-style frozen custard, the shop sells “puppy pops” made from yogurt and baked treats called Squirrels.