Winter Dining on Upper Cape Cod

Winter months are for candlelit dinners, snuggling by the open fire and great meals at our best local restaurants. Check out our Top Six (6) places to enjoy year-round dining in wintery Falmouth. Sure you are dreaming of bare feet in the sand, but strap on your Bean boots and check out the great grub served on Cape this winter.

Water Street Kitchen


Next door to us here at the Woods Hole Inn, you will find the world-renowned Water Street Kitchen & Public House. Owned by locals Molly and Chelsea Doohan, this savory stop is a must visit when you come to our area.  Also led by Molly’s husband John Wilson who runs a scratch kitchen, every bite will astound you with deft originality.  Start with the bluefish pâte and order the home baked sourdough bread, for sure. 


John’s take on seafood cioppino is also a must try served with black bread and squid ink. You will feel yourself in the hands of a master with every savory bite.

In addition to the fine dining, you will love the intimate Cape decor plus water views from every table. An ocean’s journey for your taste buds and a great way to kick off a delightful Cape weekend.

Quicks Hole Tavern

Quicks Hole Tavern

Also a short stroll from Woods Hole Inn, Quicks Hole Tavern will wow you with a great selection of on-tap craft brews and the best burger in Falmouth. Famous appetizers include crispy brussels sprouts and a unique twist on crispy bacon called “Pig Candy.” All that while enjoying the sunset over the ferry terminal where the hustle and bustle of boats and passengers make for excellent people watching all year long.


New to the menu this winter is chef Nat Summerton’s signature dish Korean bouillabaisse, a must-try when you visit Cape Cod. Before you leave, order their “Bag of Donuts” which come to the table hot with delicious dipping sauces and make great leftovers the next day.

Bonus, stay at the Woods Hole Inn and try the spectacular beers on tap at a deep discount. Learn more!

Osteria La Civetta


Thinking of taking a trip to Italy? This local favorite will definitely take your taste buds there. Open year-round, this cozy Italian bistro is situated on Falmouth Main Street with windows opening onto the streetscape. Led by husband-wife team Sarah and Andrea of Northern Italy, the house pasta is hand-rolled daily with truly authentic Italian sauces.

Osteria Food

Check out the Pesto Genovese, artfully plated with shaved Parmesan and fresh basil tendrils.  For dessert, you can not leave without the Chocolate Salami, a delightfully original dish.

Chapaquoit Grille


On a back road in West Falmouth hides one of Falmouth’s finest local secrets, locals call it Chappy Grill. Wood-fired pizza is just the start here, and we recommend trying it as an appetizer before diving into their main courses like the excellent grilled salmon, mushroom risotto, and linguine pomodoro. The service is spot on, the cocktails on point and you will see plenty of locals who flock to this place year-round in droves.


Once you step inside, prepare to be welcomed with warmth, great food and some of Cape Cod’s finest service.

Check out the penne a la vodka, a classic favorite.



The newest addition to the Falmouth foodie scene is Estia, a stylish space serving authentic Greek cuisine from a local family with Greek roots. Formerly a bank, this large urban space features 180-degree windows with a wonderful street view of historic Main Street. Try their coal-fired pizza which locks in a smokey cheese combined flavor in every bite. We also recommend the kabobs over Greek salad, delicious as well as great value.


Also try the Mediterranean- style grilled octopus or perfect bite-sized lamb lollipops. You are sure to leave Estia with a warm smile, secure in the sense that you have dined at one of Falmouth’s finest.



This cheery, family-friendly location features delicious Italian food with a Cape Cod twist. Located in the heart of Mashpee Commons, about a twenty-five-minute drive from the Woods Hole Inn. We highly recommend their garlic mussels and be sure to use their thick slices of bread to mop up the buttery broth.

Siena food

Siena is also known for traditional Italian chicken parmesan, and you should not leave without an order of their homemade tiramisu with its unique espresso finish.

So there you have it, our locals secret top six (6) best places for year-round dining on the Upper Cape. Visit the Woods Hole Inn and our front desk will fill you with recommendations of other exciting fun  Things to do in the Winter on Cape Cod.