506 On the River Inn

In order to celebrate a recent success at work, I spontaneously decided to book an overnight in Woodstock, Vermont this past weekend. Chris and I had been planning to do a day hike on Saturday anyway, and because Vermont is somewhat in-between “leaf peeping season” and ski season, hotel rates were too good to pass up. After a little research, I decided to book the 506 On the River Inn (it had amazing reviews and beautiful photos on the website.)

We left Boston around 8am, and made the 2.5 hour drive to Windsor, VT where we pulled up to the trailhead for Mt.Ascutney. I loveeed this hike…mostly because it is a very steady 3 mile incline up to the summit, so I was able to get my beloved dose of cardio in. At the top of the mountain, there is a 25 ft. observation tower, where we experienced amazing views of the Green and White Mountains. We had to be extra careful on our journey down, since the trail is covered in leaves and slippery! In total, the 6 mile round trip took us approximately 3 hours. If you want to know exactly what I brought for this hike, view my “City Girl on a Day Hike” packing list!

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At 4pm, we checked into the hotel. Think cozy Vermont + Restoration Hardware + Halloween night and it pretty much sums up the atmosphere of the 506 On the River Inn last Saturday! The staff had the placed tricked out with pumpkins, apple cider, candy bowls and Halloween-themed music playing. The hotel is beautifully decorated and homey, with a rustic bar, a country-style kitchen/restaurant and large fireplace/sofas. I couldn’t stop taking pictures of the decor…I overheard another guest saying that the hotel is owned by a couple, and the wife took on the role of interior designer. She did a great job…take a look!





Before heading out to dinner, Chris and I ordered drinks and appetizers from the antique bar and sat by the fire to relax. A few people our age were hanging around the coffee table, playing cards and enjoying spiked cocoa. Does it get any more rustic-New England than that?





I fell in love with the beveled subway tile in the country kitchen (breakfast was complimentary in the morning – fresh juices, Vermont coffee, eggs, bacon, fresh fruit, pastries…the works.)



Needless to say, we didn’t want to leave when it came time to check out at 11am. Luckily, we had turned the clocks back and ended up earning an extra hour in the morning. So moral of the story, if you’re looking for a super relaxing and cozy getaway, I would highly recommend looking into the 506 On the River Inn.

Not into hiking? There is plenty of other things to do near Woodstock (horseback riding, shopping, beer tasting) – the Inn does a great job of listing out weekend activities here.

On Sunday, our next stops included the Vermont Flannel Company and Simon Pearce.  Tune in for my next post – Ill be sharing photos from the Simon Pearce Flagship Store and Restaurant 🙂



  1. Dara November 10, 2015 / 7:59 pm

    There is a River Inn Hotel just around the corner from me in DC, I did a double take when I saw the name of this post! The River Inn you went to looks so comfy too! I’m glad you had a great weekend! XO

  2. slowitdown November 11, 2015 / 1:51 pm

    I will have to check it out Dara! I have family outside of Annapolis and love to visit DC. The company that owns the Inn on the River in VT actually owns several hotels in East Africa as well – pretty unique! Curious as to how they decided to open an Inn in rural Vermont 🙂

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