With Troy finishing packing up the last of his belongings from his childhood home this past Saturday, that left our Sunday wide open for a daytime adventure. Given that he was still pretty spent from all the driving and boxing/unboxing in recent days, he generously stepped back and let me take full control of how and where our day would be spent so he could just sit back and enjoy the car ride (and whatever dining locations I had planned!)
We kicked off our morning with breakfast at Wells Provisions in Charlemont, Massachusetts – who were having a maple-themed Pop-Up in honor of all the sugar shack events happening in and around Western Massachusetts these past few days. While Troy enjoyed a maple-soaked pulled pork Benedict, I was in heaven once I poured warm syrup over my fresh chicken and waffles while sipping a cardamom-infused lemonade.
And of course, I grabbed some maple cream beignets for the road – because you best believe we had some driving to do!
Once we were well-fed and hydrated, I made the 90 minute drive (from my apartment – although it took a little longer from Charlemont!) up north to Bennington, Vermont. There was a very old, very historic, very abandoned and very spooky building I had wanted to see and snap photos of given the dark and gloomy weather, but much to my delight – it happened to be directly across from another historic landmark that we ended up spending quite a bit of time exploring, too!
Bennington itself, while one of the most populous towns in Southern Vermont, still manages to maintain a very cute and very quaint charm, especially in it’s downtown area. It’s also full of historical monuments, museums and markers which isn’t all that surprising considering the town was founded in 1761 and is where the Battle of Bennington took place in 1777.
But Troy and I bypassed the battle monument and instead made our way to the Bennington Centre Cemetery, next to the First Congregational Church. This cemetery, the oldest in Vermont, serves as the final resting place for Governors, military personnel, the first African-American to graduate from Yale University and a victim of the sinking of the Titanic – just to name a few – and is also where visitors can find the grave of poet and playwright Robert Frost.
There’s a lot of helpful markers located around the grounds to guide visitors and provide them with more information about some of the notable figures buried there. We were absolutely fascinated as we walked around!
And right across the street from the cemetery was the structure I had originally wanted to see – the remnants of the former Walloomsac Inn! Opened as a tavern in 1771, the inn hosted a number of Revolutionary figures and former presidents including Thomas Jefferson and James Madison. After becoming a private residence for some time, the property was ultimately abandoned in 1996 after it’s last owner had passed away and has been sitting quietly, being overtaken by the elements, ever since.
Although I’d read that the property was recently purchased in 2025 and is scheduled for renovation/repairs, we didn’t see any evidence of any work being started or in progress while we were there. Many of the windows are broken, and the shutters were loosely banging against the wood in the wind, but I can definitely see the potential in there. It’s such a cool building!
By the time we were done snapping photos and pointing out every thing we could see that caught our attention and interest, it was time to head back home to get ready for the work week ahead. As always, I took the back roads to get us to the Pioneer Valley while pointing out some other locations I’d love to head back to check out soon.
Overall, it was such a fun day spent outdoors surrounded by unique and unexpected finds – which is the best way to enjoy a Sunday, in my opinion!
xo
Coffee & Chiffon 