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Things To Do

Double Dragon Inn

59 Massachusetts 6A, Orleans, MA 02653

This late night spot is a local favorite! We've spent many nights in their tiki bar, slurping down Head Hunters and Scorpion Bowls with our favorite bartender Patrick. If you're looking for food, try their scallion pancakes and crab rangoons. They never disappoint!

Land Ho!

Massachusetts 6A, Orleans, MA 02653

A genuine Cape Cod hang out, with a charm and character all its own. Unpretentious seafood classics, salads, sandwiches & beers on tap offered in a pub-like atmosphere.

Las Chidas

34 Massachusetts 6A, Orleans, MA 02653

Great tacos with an even better tequila selection. What else do you need?

Mac's Shack

91 Commercial Street, Wellfleet, MA 02667

This local favorite offers all the summer feels: the crunch of clam shells beneath your sandy toes, the warm buzz of happy people, and the sounds of ice hitting the glass as cocktails flow. Here you will enjoy all the seafood classics + sushi! Fun Fact: All the fried seafood dishes are gluten free!

Pleasant Lake Pizza Shark

403 Pleasant Lake Avenue, Harwich, MA 02645

Located in a historic building from the 1800's, this little spot serves THE BEST pizza in town. Make sure to tell the GM that Rail Trail sent you!

Hole In One Breakfast & Lunch

98 Massachusetts 6A, Orleans, MA 02653

Informal, family-run restaurant & coffee shop serving a full breakfast and lunch menu daily plus hand-cut donuts, cupcakes & pastries. Must try their Nanny's Benedict or a build-your-own omelet!

Hot Chocolate Sparrow

5 Old Colony Way, Orleans, MA 02653

A popular local shop offering coffee, desserts, ice cream & candy from early till late. This cafe is recognized Cape-wide, their chocolate is sent all over the country, and their coffee, desserts, and fudge have been voted #1 numerous times in various local surveys.

Coast Guard Beach

2 Ocean View Drive, Eastham, MA 02642

We walk the bike trail from the Eastham Visitors Center down to Coastguard Beach multiple times a week. It's a historic beach on the East Coast and we highly recommend checking it out. From Coast Guard parking lot, behind the former Coast Guard Station, you can take a pathway that leads to the bicycle trail bridge which overlooks the Nauset Marsh. It's one of our favorite views on The Cape. Take a look at the website for fun facts and a brief history.

First Encounter Beach

Eastham, MA 02642

First Encounter Beach is known for its vast low tides and sand dunes. During low tide, visitors can walk as far as a mile out into the bay. First Encounter Beach's unusual name comes from the fact that the beach was the site of the first encounter between the English Pilgrims and Native Americans, specifically members of the Nauset Tribe.

Chatham

Chatham, MA

Chatham is a seaside town right at the elbow of Cape Cod. With its picturesque lighthouse, stunning beaches, and quaint Main Street, there is no shortage of things to do.

Provincetown

Provincetown, MA

Provincetown is at the northern tip of Cape Cod. It was the first landing place of the Mayflower in 1620, commemorated by the towering Pilgrim Monument. Numerous galleries, restaurants, nightclubs, cabarets and specialty shops are clustered on and around lively Commercial Street. Be sure to check out an authentic Portuguese bakery and a drag brunch if you get the chance!