Celebration Events
We are hosting a special meal each evening and would love for you to join as many as you'd like!
π Come-and-Go Pizza Dinner
Kick off the weekend at Chatham Pizza Shark. Swing by whenever you arrive β no schedule, just good pizza and good company.
π 637 Main St, Chathamπ¦ Clambake + Nauset Beach at Dusk
Join us at our vacation home in Brewster for a proper New England clambake. Time TBD β details to follow. Afterward, we'll head to Nauset Beach to see the Atlantic at dusk.
π 53 Old Bog Rd, Brewsterπ₯ Anniversary Dinner
Our closing celebration dinner, held at the hotel.
π‘ The Wayside Inn, ChathamNearby
Everything below is a short stroll from the Wayside Inn along Main Street.
Candy Manor + Kate Gould Park
Website βPick up something sweet at Candy Manor, then stroll back into Kate Gould Park to enjoy your treat in the shade. A Piana family tradition with the kids.
The Chatham Squire
Website βOne of our favorite haunts for a mid-afternoon break from shopping. Head to the bar and grab a drink, a bowl of clam chowder, or steamers.
Yankee Ingenuity
Website βA wonderful eclectic gift shop, just a short stroll from the hotel. Great for browsing.
The Black Dog
Website βThe brand is synonymous with Martha's Vineyard and Cape Cod. The Piana family has no shortage of Black Dog apparel β now you can add to your collection too.
Breakfast
Hangar B
Website βBreakfast and lunch at the Chatham Municipal Airport β a fun, only-on-the-Cape kind of spot. Watch small planes come and go while you eat.
JoMama's NY Bagels & Coffeehouse
Website βOne of our favorite spots for bagels and coffee in Orleans. A great reason to head up Route 6A in the morning.
Lighthouse Cafe
A quaint little diner serving the breakfast classics. The first time we had blueberry muffins warmed on the grill β you won't forget it. Come hungry, come with cash.
Lunch
Mac's Seafood
Website βA Piana family staple and an amazing menu for seafood lovers. We have a feeling the family will be heading here Tuesday for lunch β you're all welcome to join!
Red Nun Bar & Grill
Website βA great stop for a bite or a drink before walking over to Veteran's Field to catch a Chatham Anglers Cape League baseball game. A perfect Cape Cod afternoon.
Land Ho!
Website βThe Orleans version of the Squire β the bar is covered in license plates and old store signs. Great for lunch, a bowl of steamers, or just a cold drink on a warm afternoon.
Ice Cream
Emack & Bolio's
A Cape Cod classic. There's a convenient location in Chatham, but our favorite is up in Orleans on Route 6A β worth the drive.
Schoolhouse Ice Cream
One of our favorites in Harwich Port. Fair warning: even the small is as big as your face.
Ice Cream Cafe
Another Orleans favorite β a reliable stop when you're up that way.
Breweries
Hog Island Beer Co.
Website βClose to our Brewster house β great patio, great drinks, and oysters. If you're driving into Chatham Sunday and want to take the scenic route, this is the stop.
Devil's Purse Brewing
Website βYou'll spot their Handline KΓΆlsch on tap at restaurants all over the Cape β but come to the source for the full lineup.
Tree House Brewing
Website βNear the canal in Sandwich β a perfect stop coming or going from the Cape. On weekends they serve delicious pizza and some of the best lobster rolls we've ever had.
Museums & Attractions
Atlantic White Shark Conservation Center
Website βThe Cape is great white shark territory, and this center does fascinating work dispelling myths and educating the public. Fun fact: Jaws (1975) was filmed on nearby Martha's Vineyard.
Atwood House Museum
Website βA beautiful museum preserving the history and culture of Chatham.
Cape Cod Museum of Natural History
Website βA family favorite β see the aquariums (including a rare pale blue lobster!), plus birding and hiking trails. Close to our Brewster house, so consider combining this with Monday's clambake.
Chatham Marconi Maritime Center
Website βExplore the history of maritime radio communication on the Cape.
Pilgrim Monument & Provincetown Museum
Website βFor those who want to make a day trip to the very tip of the Outer Cape. Climb the tallest all-granite tower in the U.S. at 252 feet for stunning views of Cape Cod Bay.