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Imagine watching the snowfall from your window at the Paquachuck Inn overlooking the bay, listening to seagulls caw and the waves crashing against the rocky shore. You have a beautiful day planned, and here is your itinerary.

Coffee, Sandwiches and More

Starting off the day with a hearty breakfast will keep you fueled and your energy up for any excursion you might be planning. Forget the granola bars and snack packs, take an hour or two at the beginning of the day to enjoy the morning bustle at a cafe and the delicious food options that Westport has to offer. 

At Wild Honey Cafe you will be met with an extensive selection of breakfast delicacies. If you have a sweet tooth in the morning, feel free to beeline to the pastry case. If that’s not really your speed, browse through the variety of salads, wraps, sandwiches, and traditional breakfast dishes to take your pick.

For a quick morning breaky, stop by Gray’s Daily Grind. Per the name, the grind doesn’t stop and if you’re in a hurry, you’re in a hurry. Sometimes all you need is a coffee and a sandwich to go to satisfy your cravings. However, if you have time to sit down, bring your furry friends by, do a puzzle inside, sit outside and listen to the stream rush – do whatever pleases you while enjoying a mouth watering breakfast spread.

Westport Woods Conservation Park

Wintertime may not always be ideal for a walking trail but this is New England so who knows, it could be 60 degrees and sunny! Westport is one of the last surviving farming communities on the coast so consider taking a walk through Westport Woods Conservation Park, one of the protected areas of the town. 

Across 82 acres you will have access to 3 miles of walking trails along which you can spot a variety of wildlife and picturesque views to document your vacation. Should you be traveling with mini adventurers, they will have plenty of natural elements to play with, and will be free to run around the entire park.

Portas Da Cidade

Indulge in the Portuguese community of Westport at Portas Da Cidade. In the last century, Portuguese farmers and fishermen immigrated to southern Massachusetts in search of work. Many of them found jobs in the textile industry on the South Shore and never left. Since then, the Portuguese communities have had a significant impact on the cuisine and culture of Westport. 

At Portas Da Cidade you can enjoy lunch, dinner or both! Open Tuesday-Sunday, make sure to stop by here for a meal during your stay in Westport. You will have the opportunity to enjoy authentic Portuguese dishes while being welcomed into a truly lovely atmosphere.

Scour their sizable menus and make sure to ask about the daily and seasonal specials. You are sure to find a delicious meal for everyone in your family and don’t be scared to ask for seconds!

Handy House

Are you interested in history, architecture or the evolution of buildings/residential houses over hundreds of years? The 1713 Handy House in Westport offers a very different experience inside a historic home than most would expect. 

You will not be met with rooms and furniture frozen in time, or antiques that once belonged to a local celebrity. Instead, the interior of the house is mainly empty on purpose. The house has not been overly restored like many other historical sites. Visitors are encouraged to explore the walls, floors, windows, doors, hinges, moldings, plaster, and other parts of its structure to see how they’ve changed overtime.

If you look close enough you’ll see changes in those elements as a timeline and experience an up close examination of the everchanging times through an uncommon medium.

Don’t hesitate, take the winter vacation in Westport, Massachusetts. It’s the perfect combination of history, cuisine, and relaxation.