Since spending our (secret) honeymoon in the middle of Vermont, we’ve loved finding weekends where we can visit again, especially in the fall. Peak season for autumn colors is usually early to mid October.
I’d say we are still Vermont-amateurs, meaning there’s many places we’ve yet to visit, but we’ve certainly crossed off a few classic sights. We’ve taken the back roads a few times while in Vermont and have yet to regret it.
Initially I wanted to find a good hike in the area (of which I’m sure there are plenty!) but we decided to “settle” for the 100-mile view at Hogback Mountain. This is technically a glorified pullout with a large gift shop. Parking can be found along the road or at a lot just past the restaurant. The view is incredible! Pictures don’t do it justice.
We waited only a long line that poured out on the street. Fortunately the weather was beautiful, sunny and crisp. The waitress sarcastically attributed the long wait times to “horrible food and the worst service.” The food was certainly worth the wait and seemed like we’d known the waitresses forever. I recommend the Berry Berry Pancakes!
This shop caught my eye while researching the area and I’m so glad we went. I love pottery and all things home decor. You can browse the shop and take a self-guided your through the workshop! They’ve got beautiful pieces for kitchen, dining, and beyond. I scooped up the cutest dish brush with holder in the signature blue and white glaze.
Shaftsbury is slightly north of Bennington a few minutes. You’ll find the Stone House tucked away on a quiet road. The property is charming and well kept. The second floor was closed for renovations while we were there, otherwise we enjoyed learning more about Robert Frost’s life and time in Vermont. (Ask for the military discount for free admission, if that’s you!)
Another 5 star view without a hike. (Don’t get me wrong, I love hiking!) Similar to the Washington Monument, you access the top of this monument. The view was fantastic. (Ask for the military discount for free admission!) The neighborhood surrounding the property is also picturesque. The “Old First” Congregational Church is down the street, if that interests you. We didn’t make it there but several other suggested we stop by.
We spent one night at the Readsboro Inn, which was a great stop nestled in the hills and trees at the bottom of Green Mountain State Forest. It’s a mom-and-pop, no frills accommodation and the only restaurant and bar in town. The owner, Stephanie, is kind and welcoming. The drive in and out of Readsboro is worth the stay.
These bridges are all over Vermont and we drove through or stopped at a few. Pictured below is the Paper Mill Village Bridge near Bennington. I was happy to follow a little trail down to the water’s edge to snap a photo or ten.
Woodstock’s downtown is easy to access and similar to other New England downtown settings. Quaint shops with art or boutique items. If I came back I would spend more time exploring other areas. If you have suggestions, let me know!
We celebrated our wedding anniversary with sandwiches from the Woodstock Farmer’s Market. Aaron recommends #27 Russell’s Big Hustle. If you want to stay and eat, there’s a small creek running behind the building with picnic tables. A fun spot with mostly overpriced groceries.
This is a fairly easy hike with a beautiful view of Woodstock. Near the top you’ll encounter some rocky bits that won’t accommodate a stroller. Other than that it’s family-friendly. It took us approximately an hour from start to finish.
In case you’re itching for some fresh maple syrup and cheese, the Sugarbush Farm is a delicious spot where you can sample all their varieties of house cheese and syrup. There’s a family-friendly trail through the trees and even a small chapel to visit. Originally built by an owner for his own nuptials, the chapel has hosted many weddings. There’s a sweet photo album of all the couples who tied the knot there. Before you leave, head to the barn in the back to learn more about how they harvest and produce the maple syrup. We’ll be coming back.
Manchester and Montpelier are on my list for our next Vermont adventure. And then maybe even farther north.
Any tips for our next weekend trip?