Fall By The Wayside…

Oh, Hello October! With a new (and my favorite!) month finally here, it seemed fitting to say goodbye to September and kick off all things Fall and foliage with a little drive through one of my favorite towns in Massachusetts- and make a quick stop at a historical, picturesque inn and restaurant on a beautiful roadway so I could snap some photos and get some fresh air.

The Wayside Inn in Sudbury is America’s oldest operating inn, having served as a tavern and boarding house since 1716. The grounds have expanded considerably since then, and now includes a nearby grist mill, chapel and one-room schoolhouse (which is reportedly the same schoolhouse referenced in “Mary Had a Little Lamb”) that are all within a short walking distance from one another.

The inn is still fully functional, with the dining room(s) open daily- and is a popular destination for weddings, anniversary celebrations, etc. The surrounding grounds, too- are almost always bustling with photographers capturing engagement sessions and senior photos at any given time.

I happened to stop by at a perfect moment, since there was a farmer’s market happening right across the street from the inn and spread out around the neighboring barn- which also serves as a gift and antique shop. Being able to pick out pumpkins and gourds with the inn’s beautiful exterior as a backdrop was an ideal way to spend a Sunday afternoon!

The Inn also hosts seasonal fairs, arts & crafts events, and so much more- and it’s particularly beautiful at Christmastime, too. Whenever I have the extra time to drive by while I’m either en route to or from Boston- I always try to make it a point to pass through the area. Even if I don’t stop to take a look around- the road itself is gorgeous and Sudbury is so charming!

The next time I visit, I’m absolutely going to grab lunch or dinner. Their menu looks phenomenal- and I love a good meal next to a fireplace- especially this time of year!


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Hi! I'm Ashley. I'm a blogger and a radio personality with a makeup and shoe addiction based out of Boston and the Pioneer Valley. These are my (mis)adventures.

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