Michele

This can get crowded on holidays and weekends, but even with crowds, it’s a nice spot for pups to cool off. My dog isn’t a fan of waves, be he does enjoy being just close enough for the water to wet his belly and feet. It’s always breezy here and a nice place to escape the heat, whether you walk in the surf, or walk among the shade a trees.

If you have a dog who loves natural scents, this is a spot for you! There are shaded paths and a wonderful boardwalk. Be sure to bring plenty of water, as there is limited shade on the boardwalk and no fountains.

There is a public restroom, but depending where you are walking, it could take a while to refill water bottles.

Beautiful nature walks for pup and peeps!

Perfect spot for breakfast or lunch, especially when it’s cold. The outdoor, dog-friendly dining area is essentially the same as eating inside. It’s fully shielded from the elements with plenty of ceiling-mounted heaters. Endless coffee, fantastic freshly-squeezed juices and a fantastic selection of dishes. Be warned, all of the dishes here are H U G E, so be prepared to take home leftovers. I particularly love the Spicy Seafood Frittata and the Strawberry Blintz! Friendly personnel and fun setting. Highly recommended!

This Red Roof Inn appears to have been recently renovated. It was very clean, and well-appointed, with a fridge, coffee maker and microwave. The hotel is off of the main road, so it was a safe area to walk the dog, and yet close enough to food, a grocery store, Dunkin’ Donuts. It’s only a 5 min drive to town center and a couple of minutes to the college. Highly recommend. It was much better than I expected for the price. We’ll definitely stay here again next time we’re in Chestertown.

While this isn’t oceanfront, the bay side view rooms are stunning with balconies. This is by far the most dog-friendly hotel we’ve stayed at (and returned to). The rooms are super-clean and modern. Dogs are welcome anywhere in the hotel, including the lounge, with the exception of in the pool. We’ve come here off-season and typically drive to the boardwalk and beach area. The staff are friendly and helpful and the rooms are all well-appointed. I had read the live music from the bar could be loud, but our last stay we were on the 2nd floor, right above the music and it wasn’t loud at all. Quite enjoyable and relaxing. Highly recommended. We will definitely return again for our off-season visits.