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Travel Guides

Once Upon A Castle: Autumn in New England

Last updated on April 11, 2018.

Our dog, Kit! She loves roadtrips too.

Today I bring you a beautiful little gem tucked away in the forests of New Hampshire. This journey here is best taken in mid-autumn, when the leaves are at their color-changing peak. It’s really one of those trips where the drive is just as beautiful as the destination, if not more. If you’ve never driven through New England in the autumn, you are truly missing out. The only cost involved to enjoy this adventure is the gas for your car. Driving through Vermont and New Hampshire is a joy in itself. Any stops you make along the way (for example, to get food), are just a bonus!

The journey to the castle

Madame Sherri’s Castle Ruins lie in the Madame Sherri Forest in Chesterfield, New Hampshire. Coming from Vermont, you would cross the bridge over the river that separates Vermont and New Hampshire. Before we get into the beauty of the New Hampshire landscape, make sure that you stop in Brattleboro for lunch atIMG_9093 Whetstone Station, one of Vermont’s infinite craft breweries. At Whetstone, be sure that you go up to the third floor roof-top bier garten. You won’t regret it. To be perfectly honest, I can’t remember how much I liked our drinks because I was so overwhelmed with the beauty of the area. The beers could have been awful (which they definitely weren’t!), but I’d still go back again and again just for the atmosphere. It was a perfect choice for that day.


Madame Sherris ForestSo now that you’ve had your drink(s) and maybe a snack, it’s time to cross the Connecticut River and make your way into New Hampshire. The forest is only a short drive from the border – and is both FREE and dog-friendly! You can park your car in a lot at the park entrance on Gulf Road. The walk to the castle ruins takes you past a small pond and is fairly easy and level-grounded.

The castle ruins

The ruins are exactly that – ruins. If you are expecting to see a grand castle, you may be disappointed. As with most historical treasures, it was suffered from fire and vandalism. All that remains is the stone foundation and a stairway that leads up over a few arches from the original building. You can read more about the story of Madame Sherri and her castle at the link at the beginning of this post.

Be careful when climbing up the stairs – these are ruins, so there are walls or handrails to help you! If it is wet or icy, please use caution and your best judgement. When you’re done exploring the ruins, don’t leave! The trails, though rugged, are worth it. We traveled along the Anne Stokes Loop and the Daniel’s Mountain Loop with our dog and I’m no sure which of us enjoyed it more! There are sections of the mountain trail that are steep, rocky, and not always well-cleared. It’s not for the faint-hearted, but for the more adventurous hiker (and their adventurous dogs).

Halfway up the mountain trail you may ask yourself why you chose this trail, but keep going. I promise it will be worth it. Once you reach the top of Daniel’s Mountain, you’ll know why you pushed yourself, and you’ll be glad you did. The views of the New Hampshire countryside are unbeatable. We reached the summit shortly before dusk, which made the clouds and landscape even better. There is a spot along the trail with some large, flat rocks, which are perfect to take a rest upon. Do it. Take several minutes to relax and truly take in the scenery before you make your way back down the mountain.

Madame Sherris Forest View

This brings us to an end of a perfect autumn day in New England. A good mix of food, drinks, and outdoor activity that will leave you wanting more. And one of the best parts? You could enjoy this whole day for merely the price of a beer at the lunch spot.

Happy travels!

Once Upon a Castle - a guide to New Hampshire and Vermont in the fall - Wanderlust on a Budget -

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  • Amy Poulton - Page Traveller

    Hey Dani,

    First off, your dog is adorable! Then also, I’m hearing so much about New Hampshire lately! Obviously somewhere I need to put on my list.

    Also, I just wanted to say that I think your blog name is perfect – this is basically my life! Will definitely be returning again for more budget travel tips etc – I feel like you’re on my level!

  • MeganCheckers

    Yay New England! I love exploring this region, growing up in Massachusetts, New Hampshire and Vermont both hold such special places in my heart. Never heard of this castle before, but I love old things and especially ruins, so I’ll have to check it out!

  • Joanna

    It must be nice to explore the ruins and imagine how the castle would have been looking like in the past, once it was in glory overlooking the lake. It’s nice that you continued on the train and ended up at the summit, resting on the rocks and looking at the superb views.

    • dani

      Yes there are several! None that really live up to the European standards, but castles nonetheless. New York has some in the Thousand Islands region. And thanks 🙂

  • C-Ludik

    Love hearing about new places like this ! I’m a truly nature lover so I would definitively love to visit forests of New Hampshire ! I love seeing the beautiful hues of colors that enter our environment. Actually, to be fair, I’m obsessed with autumn anywhere in the world. It’s my favorite time of year. Halloween. Crunchy leaves. Pumpkins. Bonfires. Colorful forests.

  • This Epic World

    Your dog looks adorable! I wish I had a dog that I could take with me to beautiful places like this one. It really looks like a perfect day out and autumn is really my favourite season. Also, I wouldn’t mind a couple of sips from that beer🤣

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