You and your canine compatriot can cruise the Chesapeake Bay in style with Watermark Cruises in Annapolis. Whether you have just an hour or want to enjoy an entire day on the water, the company has you covered. Enjoy a quick 40-minute trip around the bay as you learn about Annapolis history, or set off on a 90-minute excursion highlighting the scenic Severn River. If you want to see more of coastal Maryland, spend an entire day on the bay with a tour to St. Michaels on the Eastern Shore. There, you’ll disembark for three hours of shopping, sightseeing, and dining along the town’s charming streets before completing the return journey to Annapolis. If your dog needs to shake off his sea legs, head to Quiet Waters Park after your cruise for off-leash playtime in the dog park or along the hiking trails.

After a day on the water, you and your furry friend can take it easy at the Graduate Annapolis, located in the heart of the Annapolis Arts District. In addition to offering first-rate rooms and amenities, the hotel welcomes visiting pups with an assortment of treats and toys from BarkBox. Fido can also meet furry friends in the outdoor dog park located on the second floor.

Spend some quality time with your hound on an outdoor adventure at Savage River Lodge in Frostburg. Located within the 700-acre Savage River State Forest, the lodge provides a year-round peaceful oasis from the distractions of daily life. In the spring, try your hand at fly fishing for trout in the cold mountain streams. Summer is the perfect time to take man’s best friend for a hike along the 13 miles of maintained trails looping through the property and surrounding state forest. Relax amid the changing scenery during the brilliant fall foliage season. Enjoy a winter escape on the cross-country ski trails, or take a snowshoe expedition with Fido by your side. Regardless of the season, pups are welcome anywhere on the property except inside the lodge and on the porches. A dog wash station is available from May through October.

From the acres of outdoor fun to the daily homemade dog biscuits given to all visiting pooches, Savage River Lodge is a doggy paradise. When it’s dinner time, Fido can savor canine casserole and mutt meatballs from the ‘Bone Appetit’ menu. After a full day, cozy up in one of the private, two-story cabins appointed with everything you and your pooch need to enjoy a comfortable night.

Experience Maryland’s coastal waterways with Ayers Creek Adventures in Berlin. Located just a stone’s throw from Ocean City, the family-owned business can introduce you to the quiet side of this bustling beach town with a kayak, canoe, or stand-up paddleboard rental. As you paddle Ayers Creek with your canine companion, he’s likely to see bald eagles, herons, egrets, and osprey nesting in the salt marsh. If you’d prefer to paddle Sinepuxent Bay, boats can also be delivered to Castaways Campground by request. Either way, you’ll get a brief lesson, water trail map, and guide to the local wildlife before you set off.

Sheltered on the shores of Sinepuxent Bay, Castaways Campground offers pet-friendly cottage and RV rentals. The property features dog-friendly perks including a bark park, bark beach, and dog wash station. Fido is also welcome to join you for a drink at the on-site Jackspot Waterfront Tiki Bar, which features live entertainment during the summer.

Ready for a Road Trip?

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