Welcome to Dennisport! I love this little town year-round, but it’s truly magical once the weather gets warmer and Old Wharf Road starts bustling with morning walkers. Whether it’s your first time visiting or you’re a regular at Clancy’s, check out our perfect day in Dennisport.
Get Active
What’s better than starting your morning with a gentle yoga flow by the beach? In the summer, Nove Yoga offers multiple classes on both Sea Street Beach and the Pelham House Resort property (you don’t have to be staying there to go). Sneak out first thing and get centered before the craziness of the day begins. Find out more information here. If running or biking is more your thing, cruise along the Cape Cod Rail Trail for a few miles before the world wakes up.
Breakfast
After yoga, pick up some breakfast from Woolfie’s Bakery to take back to the family. Woolfie’s is famously known for delicious muffins the size of your head and other fresh-baked pastries. My go-to is the sausage, egg, and cheese sandwich. They also have the best iced coffee with coffee ice cubes! Woolfie’s is a takeout spot and gets VERY busy in the summer months, so order online the day before to beat the lines. If a sit-down restaurant is more your scene, hop over to The Sailing Cow. They have nostalgic music that’ll take you back to your college days and a great deal on their kids’ menu. Order some massive blueberry pancakes and people-watch the morning walkers on Old Wharf Road.
Beach
Now that you’re back from breakfast and have the sunscreen on, get ready to hit the beach. Luckily, Dennisport has many to choose from. My personal favorite is Sea Street Beach. It has an elevated view of the many jetties along the coast and there’s a fun “locals” vibe. Going to Sea Street Beach requires navigating stairs, so if you’d rather step straight onto the beach, check out Glendon Road Beach. Another great option is West Dennis Beach, which is a mile long with tons of parking. You can also check out some exciting windsurfing there on the right day.
Lunch
I highly recommend stopping by Bandera’s Market and Deli for sandwiches and taking them to the beach with you. My girls love ordering the kid’s banana nutella sandwich as a treat. Their potato salad is also delicious. If you’re looking for more of a sit-down restaurant, The Doghouse has an expansive menu (not just hot dogs) and “frose” slushy coolers that are A+ on a hot day.
Activities
After the beach, head over to Holiday Hill Mini Golf for a little friendly competition. The course is dotted with beautiful hydrangeas and nautically themed holes that give a quaint Cape Cod feel. It’s also less crowded than other courses in the area, which is perfect for young kids.
There are plenty of options for shopping in the area so you can stock up on souvenirs. Cuffy’s has been newly remodeled and is an absolute emporium for all things Cape Cod. They are stocked from floor to ceiling with the coziest signature Cape Cod sweatshirts in every size and color. You can find anything from coffee mugs and key chains to books, puzzles, and stickers.
Another shopping hotspot is Main Street in nearby Harwich. Main Street is a quaint shopping hub lined with coffee shops and gift stores. Dr. Gravity’s Kite Shop is an eclectic store for kiddos, Reed Books is a great local bookstore, and Buoys on Main is a staple for unique gifts.
Dinner
Now that you’ve worked up an appetite, there are many delicious restaurants in Dennisport to choose from as you reflect on the day. If you’re looking for an upscale ocean view, look no further than The Rooftop at Pelham House Resort. Their rooftop view of the water can’t be beat. Interested in something more casual? Check out Cleat & Anchor for some amazing barbecue dishes or Southside Cantina for some tacos and live music.
Dessert
Wherever you end up for dinner, save room for ice cream at Sundae School! You’ll instantly be transported to yesteryear with friendly service, delicious ice cream, and the signature “Sunday School” paper hat for the kiddos. The perfect way to end a day in Dennisport is with a waffle cone of your favorite ice cream flavor. Sprinkles included.
If you’re looking to expand your vacation beyond Dennisport, check out this article on fun things to do in the summer all over the Cape. What are your favorite spots to visit in Dennisport? What town should we feature next?
