Two of the three places I will share with you in this post are within walking distance of the cottage - which makes them even better :).
I heard about the first place from a local contractor and boat owner and when we arrived, we knew we had found a local gem. The Summer Shanty is hidden in the Bass River Marina - a five minute walk from The Pines. We arrived through the door from the parking lot into a happily crowded room with live music playing and the dining deck over the marina calling to us beyond open doors. Once on the deck, you discover another treat - a beautiful lawn bordering the marina where groups of friends lounge in Adirondack chairs. Find a chair and a server immediately arrives to take your drink order - you can also pull up a table and eat dinner right on the lawn. Time it right and you can have your very own front seat for the spectacular Cape Cod sunset show.
The second place is the closer to West Dennis beach but because of how it is situated also has a great sunset view over the marshes. The Sand Bar is a funky little beach bar and pub on Lighthouse Road with live music. It is very casual and old Cape feeling and caters more to the younger crowd than The Summer Shanty.
The Susuit Harbor Cafe is a seafood shack also hidden in a marina on Sesuit Neck in Dennis on the north side of the Cape and you might need to ask for directions from a local. It has a large dining area with picnic benches out over the water - you order your food inside and take it out yourself. Nothing fancy but the view is worth millions of dollars - literally. It is BYOB so bring your favorite drinks to do with the great lobster rolls and enjoy the view!