The Wayside Inn

Looking for a fun and festive day trip from Boston this weekend? Longfellow’s Wayside Inn is the perfect spot to visit this time of year for a step back in time and some holiday cheer.

I first visited the Wayside Inn years ago when I attended a retirement party there, but I have been a fan ever since, especially during the holiday season. It is the oldest operating inn in the country and has been opening its doors to guests since 1716.

The inn itself is historic and beautiful, and when graced with blue skies and adorned with Christmas decorations, it is really something special. Holly abounds nearby, and the inside of the inn is warm and festive.

The Tap Room at the Wayside Inn is the perfect place to enjoy a drink and a warm fire. The nation’s first cocktail, a Coow Woow, was invented here, and they still serve it to this day.

We of course had to give a Coow Woow a try. . . and I would not recommend it unless you needed its contents to light a fire or lamp. Woow.

The ingredients in a Coow Woow are simple, ginger brandy and white rum, and it is strong! It’s easy to imagine our forefathers getting through cold nights with this concoction, but I’ll stick to the more tame Meetinghouse Punch, which was a blend of beer, rum, and sugar.

It’s easy to linger in the Tap Room for the afternoon, and we met some very nice people planning a trip to Ireland whilst there. The Wayside Inn is not just a step back in time, but it is also a very classic New England place for food and drink, an excellent day trip from Boston.

Parts of the inn are preserved in a museum-like fashion, allowing guests a glimpse into the early days of the inn,

While the inside of the Wayside Inn is spectacular and homey, the land it is on as breathtaking. I love every second of blue sky and fresh air I can get in the country, and the Wayside Inn has it all, from rolling green hills to a lake to the most beautiful chapel.

When visiting the Wayside Inn, you can breathe in the smell of pines and enjoy the crunch of leaves and pine needles under your feet, all before digging into a delicious hearty meal paired with old fashioned drinks. The inn also often has events and special packages making it a fun little getaway from Boston.

I love this space and am glad we took an afternoon from the busy holiday season to escape to Sudbury in the 1700’s.