Dennis is located in the Mid-Cape, sharing the "bicep" with Yarmouth, as well as sharing the Cape Cod Baseball Team, Yarmouth-Dennis Red Sox. There are five distinct villages in Dennis, all with a variety of attractions & activities, along with great beach access on both the North (Bay) and South (Ocean) side.
8:00am: Breakfast at The Red Cottage
The Red Cottage has been popular with summer travelers and year-rounders alike since it opened in 1951, when it was strictly a seafood restaurant. Located in South Dennis, this is a great place to stop & grab an inexpensive, home cooked breakfast. This diner style atmosphere is about a ten minute drive to either the North or South Side beaches.
9:00am: A Day at Mayflower Beach
One of the more popular beaches on Cape Cod, if not in Massachusetts, Mayflower is famous for their long stretch of white sand, calm currents, & small pools created at low tide. There is a long boardwalk from the parking lot to the beach which is an underrated amenity, especially if you are carrying a large load from your car. Because of its popularity, we recommend getting here around 9am to guarantee a $20 parking spot ($25 on the weekends). They also have a snack bar if the urge for ice cream or something fried hits you.
Lunch: Lobster Rolls at Sesuit Harbor Cafe
About a five minute drive from Mayflower Beach in East Dennis is the Sesuit Harbor Cafe. What used to be a hidden gem off the beaten path, has become a foodie destination due in no small part to its Instagram-famous Lobster Roll! They offer very rustic & casual decor with picnic tables over looking Sesuit Harbor. When you drive up there will be a parking lot attendant waiting for you, tell them you are there for a lobster roll & they will let you right in.
2:00pm: Kayak or Paddle Board Along Bass River
Bass River, an estuary that acts as a natural town border between Yarmouth and Dennis, is a great area for outdoor activities like fishing, kayaking, and paddle boarding. Conveniently located right on Route 28 is Bass River Kayaks for all your boat & board rental needs. For less then $30 you can rent either a kayak or paddle board for 90 minutes to take you up and down the river with plenty of moments for the perfect Instagram shot along the way.
Dinner: Oyster Company Bar & Grill of Dennisport
This seafood restaurant is located in Dennis Port or Dennisport (depending on who you ask) which is the tourism hub of Dennis with many options for dining, activities, and lodging. It's not too hard to convince customers of The Oyster Company on how fresh their oysters are seeing that the owner, Greg Burns, also owns an oyster farm on Quivet Neck Creek in East Dennis. This is a favorite of summer travelers as well as locals, which says a lot.
9:00pm: Live Music at Cleat & Anchor
About an $8 Uber ride away is Cleat & Anchor, a popular night time hot spot with Live Entertainment and a patio that has outdoor seating and a few lawn games. Cleat & Anchor has a great beer selection is perfect for large groups. The line starts are 10:00 so it's recommended to get there around 9:30pm to avoid waiting outside. This is also a great area to bar hop as well with Chapin's and the Sand Dollar Bar and Grill directly across the street.