Great oceanfront beach for a nice beach day if you are staying in Orleans. Because it's a holiday weekend, we recommend getting there before 10AM to beat the line
Features two championship courses, Port and Starboard, set against the scenic backdrop of Cape Cod, offering a diverse and challenging golf experience in a welcoming environment with modern clubhouse amenities.
Stop by downtown Chatham for boutique shopping, coastal eateries, and the picturesque Main Street
The Beachcomber in Wellfleet is an iconic oceanfront restaurant located right at the top of Cahoon Hollow Beach. This is a very popular destination, so we recommend getting to the beach EARLY as parking is very limited. If you would rather go for a sunset Goombay Smash and oysters, you might have better luck with getting a spot around 4-5pm as beachgoers are packing up for the day. If you want to purchase one of their famous sweatshirts, there is a shop at the restaurant and an official Beachcomber store down the road at 1446 US-6, Wellfleet, MA 02667.
The Cape Cod Rail Trail is a scenic 25.5-mile biking path that winds through surrounding towns of the outer Cape. We recommend parking at the Chocolate Sparrow and getting on the bike path from there. There are several cycle shops nearby for rentals, including Orleans Cycle and Idle Times Bike Shop.
Boating, sailboat, and paddleboard rentals
Handful of fun hiking trails with beautiful scenery. Check out: https://www.alltrails.com/parks/us/massachusetts/nickerson-state-park
Pickleball courts
Waterfront park on Pleasant Bay for walks & hiking
Fishing and boat charters
Seals & tours of Pleasant Bay
Paddleboard and surfboard rentals
Best burritos in Cape Cod :) There is also a location in Chatham
Great breakfast and lunch spot with delicious coffee, sandwiches and NY bagels
Amazing coffee, chocolates, and sweet treats. An absolute must if you are staying in Orleans!
Get the dirt bombs and cranberry almond poppyseed muffins
Cozy local spot with yummy breakfast and lunch offerings
Best donuts on the Outer Cape. There is also a location in Eastham
Waterfront lunch and dinner spot on the border of Harwich and Chatham. Plus, Courtney used to work here during the summer! We recommend making a reservation in advance as it tends to book up fast.
This is where the welcome party will be, but it's a great spot to grab a beer after a long bike ride, or catch some live music!
Amazing clam chowder and lobster rolls
Delicious lobster rolls and seafood, and situated right on the bike path
Historic sea Captain's landmark with great indoor/outdoor dining, live music in pub
Fun taco spot right on the Cape Cod Rail Trail bike path in Brewster!