Grand Millennial's Fall Travel Guide to Vermont

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From the moment we walked into this charming inn we felt like family. Nestled away in the town of Bennington Vermont, is the pretty and quaint bed and breakfast, Four Chimneys Inn (see the 4 chimneys!). From its soft floral and damask wallpapers, to the chandelier above the grand staircase, or the beautiful bay windows, and intricately trimmed fireplaces in the rooms, this place is a true Grand Millennial’s dream!

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It was actually extremely therapeutic to switch it up from our normal boutique or grand hotel travel style to a bed and breakfast. After staying here, I’m going to be trying this out more, although the others will have extremely high standards to live up to to compete with Four Chimney’s Inn, their historic architectural design and their lovely staff.

When you arrive, you pull around to the entrance, beaming in classic charm with its true red door and holiday décor. We were greeted by their lovely inn keeper Kim, who took care of our dinner reservations, gave us a run down on the area’s highlights, and showed us to our room- which has a stunning bay window bench and gas fireplace. It’s seriously so pretty and everyone here was so genuinely kind.

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Lynn and husband Pete are the owners and can I just tell you, Lynn is so talented! From their floral garden, to the gourmet breakfast she makes (see pancakes below!), and her knowledge of the town, you can tell Lynn truly loves what she does…and that my friends is making you feel right at home in your home away from home for your stay.

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Clearly, I highly recommend a visit to the Four Chimneys Inn for a truly relaxing and special vacation and I think there’s no better time to visit this town than in the Fall, although I hear their Summer’s are quite beautiful too. I just love the “leaf peeping” season and Bennington Vermont surely does not disappoint when it comes to seeing an array of beautiful Fall colors and picturesque mountain views at all different elevations. More on the historical, beautiful places to see and photo opp spots here plus my travel tips for catching the foliage just right.

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Be sure to also check out Hildene, the Lincoln family home. It is breathtaking and the mountain views from the garden are incredible. It was nice to see the periodical furniture and floral feminine design palettes in the ladies rooms, similar to the Biltmore. The moldings and detailing were just incredible throughout. Fun note, you can also get married here and in the Fall would make quite the beautiful backdrop! The photos below were taken inside one of the ladies rooms and out front by the pretty mums and old fashioned car they had out front. The tea set reminds me of my great Grandma Pearls set from London that I inherited and the car similar to one of my Pop-pops when he collected antique cars.

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Let’s talk local food for a minute though, because Vermont definitely didn’t disappoint in that area. Anytime Mark and I travel we seek out an authentic Italian restaurant, being that we are Italian! I guess it’s one of our traditions, and as a grand millennial, that’s something I really appreciate and highly recommend doing when you travel. There’s just something so special and nostalgic about creating new traditions together. So in downtown Bennington we found the BEST Italian restaurant, Allegro, which was recommended to us by the inn. The eggplant parmesan meatballs were unlike anything I’ve ever had before, and the Rigatoni with chicken and spicy tomato cream sauce was out of this world good- just the right amount of spice! They also proudly use seasonal ingredients from local farms too, which I love!

A couple other places for good food to check out would be Pangaea for an upscale, cozy and delicious meal (the filet was melt in your mouth good), as well as the Tap House at Catamount Glass for a casual lunch spot with great craft beer, soup and sandwiches, sure to warm you from the crisp Autumn air we experienced while there (weekend of October 18th 2019).

What can I say, other than Fall in Vermont is a dream come true, and with a relaxing stay at the Four Chimney’s Inn, you’ll leave wanting to surely come back for more. I can’t thank them enough for hosting us over the weekend! Follow them on Instagram for more Vermont Travel Inspiration here.

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