Vermont Fall Road Trip - 320 sweet miles

Vermont Fall Road Trip - 320 sweet miles

Discover the ultimate Vermont fall road trip with our curated itinerary covering Stowe, Peacham, Woodstock, Grafton, Manchester, Dorset, Middlebury, and Burlington. Find the best scenic routes, top attractions, must-visit shops, delicious dining, and cozy places to stay—perfect for experiencing Vermont’s legendary autumn foliage!

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6 Vermont Towns - 320 sweet miles

6 Vermont Towns - 320 sweet miles

Discover the ultimate Vermont fall road trip with our curated itinerary covering Stowe, Peacham, Woodstock, Grafton, Manchester, Dorset, Middlebury, and Burlington. A few of the best scenic routes, perfect for experiencing Vermont’s legendary autumn foliage!

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Summertime Farmer’s Markets

Summertime Farmer’s Markets

Talk about where small towns really shine - the summertime farmers market. This sets the farm-to-table game on an entirely new level! Here are a few of the markets, dates & times, and websites for some of our favorites. Make sure you check them for up to date times and locations. Some are open all year, but move indoors.

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Woodstock Taxes

Woodstock Taxes

It is just the hash reality of living - taxes. Here is a quick summary of what you will find in Woodstock, Vermont. The town has a significant tourist economy, so sales taxes drive revenue to an extent with a 1% local tax added to the state.

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Quicktake: Woodstock, Vermont

Quicktake: Woodstock, Vermont

Step into downtown Woodstock and you'll find yourself transported to a quintessential New England village. I know that term is thrown out with abandon, but seriously, this is the town it was crafted for. The streets are lined with charming 19th-century architecture, creating a picturesque backdrop for your Vermont travel adventure.

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Let’s talk about the weather in Woodstock, Vermont

Let’s talk about the weather in Woodstock, Vermont

Woodstock is a dream for those who adore the ever-changing tapestry of the seasons. As we take a look at the average weather patterns of this quintessential New England town, you'll discover there are always perfect activities to indulge in, no matter the time of year.

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A Nomad’s Dilema

A Nomad’s Dilema

The small towns of Vermont are popular destinations year-round with a robust short-term rental market. Platforms like Airbnb offer numerous fully furnished monthly rentals, making it feasible for visitors to settle in comfortably for extended stays. However, many of the towns have implemented regulations that cap the number of days short-term rentals can be rented out annually, except in certain zoning districts, or require stays to be longer term. Obviously this constrains supply but we certainly understand the . .dilemma. We visited on small town that experienced an entire neighborhood, with once exception, flipping to short term rentals. When none of your neighbors are local - it somewhat defeats the charm and draw of the town in the first place.

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