Visiting Vermont in Autumn

Visiting Vermont in Autumn had been something on my bucket list for many years, and this year, following a trip to Boston, we decided the opportunity was one we couldn’t miss! So we hired a car and drove two hours from Boston to Woodstock; a town that I’d researched as a quintessential and typical Vermont town with plenty of character and beautiful foliage and scenery for us to enjoy.

Just as I’d imagined, the town of Woodstock was utterly charming. It was as though it was caught up in a time warp, with shop exteriors and restaurants all seemingly unchanged in the past 5o years. Like something from a film set, it was an Autumnal wonderland.

Charlie and I checked into 506 On The River Inn for two nights and it was the perfect base. A cosy B&B with an incredible Bistro; 506 Bistro, as well as friendly staff, open roaring fires and even a ‘Smores pitt for toasting marshmallows on clear evenings.

Our days were spent exploring the local area; long walks admiring the foliage and trying out the town’s selection of coffee shops and bakeries – there were plenty to choose from and each had their own individual charms.

What I adore about American towns such as Woodstock at this time of year was that each doorway was carefully decorated to celebrate the Autumn season, or Fall season I should say, and trust me; there were plenty of photo opportunities for posing on Pumpkin – laded porches!

506 Bistro at On The River Inn

Seasonal dishes fill the menu at the cosy and bustling bistro located within our hotel; 506 On The River Inn. The large dining room complete with open roaring fire was the perfect place to settle in after a day exploring. We started off our evening with a seasonal cocktail; my Pumpkin Latteini was an absolute delight, made all the more wonderful by the incredibly jolly staff who took the time to give us tips on things to see and do while in Woodstock as they took our orders.

Craving comfort food, we had Chicken Wings to start before enjoying a burger and a fillet steak for our mains; and they certainly hit the spot! The dishes were beautifully presented and seasoned beautifully, exactly what we were craving.


Just a few minutes from the town of Woodstock, 506 On The River Inn is a family run hotel located right on the banks of the Ottauquechee river. With just under 30 rooms, there’s a cosy relaxed vibe and plenty of small details that make it a wonderful place to stay; ranging from the free cookies and home-brewed cider to the farmhouse kitchen breakfast, it almost feels like a home from home. The boutique inn is decorated with antique ornaments collected by the owners, who also have hotels in East Africa. There’s also a swimming pool, games room for the children and a library for guests to enjoy.

Discover more from On The River Inn here.

During September and October especially, there’s plenty to do in Woodstock. Charlie and I also visited a nearby town named Quechee to dine at ‘Simon Pearce’ restaurant that had been recommended to us – the restaurant was located inside the glass making workshop and pottery, giving visitors plenty to see before or after their delicious meals.

There are also a variety of farms that visitors to the area can discover, as well as farmers markets and plenty of hiking paths to truly discover the local area.

Head over to my Youtube for my Outfit Diaries filmed in Woodstock for more!