The Best Family Day Trip in Beautiful Woodstock, Vermont

by | Family, Travel

Looking for a budget-friendly family day trip in New England? We spent a gorgeous day in the beautiful Woodstock, Vermont area! Here are the highlights of our fun, family day!

Note: This post is not sponsored in anyway by the town of Woodstock or any businesses.  These are our true favorites and highlights of exploring the area!

I love to travel and thankfully, I married someone who loves exploring as much, or probably more than I even do!

It has always been important to us to show our kids as much of the beautiful country we live in as possible.

As they are getting a little older, it is so exciting to start taking some bucket list trips!

One of those trips is a New England tour in the fall!  As it turns out, we aren’t really “tour guide” kind of people, though, so we put together our own trip and one of the areas we decided to visit was the beautiful town of Woodstock, Vermont.

It’s no wonder that Woodstock, Vermont has been called the most beautiful town in America.  We quickly discovered why.

In fact, the whole area is just as picturesque as you’d imagine small-town Vermont to be in the early fall.

The leaves were just starting to turn and the air was crisp enough to let us know fall had begun, but not too cold to be to enjoy the beautiful outdoors without bundling up!  Literally, perfect weather in a perfect place!

Lodging in Woodstock, Vermont

A unique experience!

The regular hotels in the area were not unreasonably priced, but definitely a little higher than we’d hoped.  Certainly, there is no lack of stunning places to stay, if budget is not a concern.

When I came across a pair of vintage airstreams, nestled out in the Vermont woods, however…it was too good to pass up!  Plus, it was super cost-effective for our family!

Travel tip with kids: Check out the Air Bnb options in the area!

I really value unique experiences and we certainly won’t lack memories from this fun stay!  While the compost restroom was definitely unique, we were never uncomfortable.  *It does help that no bears showed up on any nighttime restroom trips!

We were able to visit first thing in the morning, explore a bit, then take out for a day in the Woodstock, Vermont area.  The next morning, the kids did even more exploring before we headed off on the next adventure!

The owners had the vintage airstream trailers stocked with extra blankets, fun games, and little space heaters that kept us toasty and cozy!

Our kids had the best time exploring the woods, gathering leaves and pretty pinecones (which we brought home and styled in a bowl!)  It was truly a lovely location and so much fun!

Hiking Opportunity Around Quechee Gorge

Great picture opportunities too!

We had a lot of territory to cover for the day, but we were so glad we made a stop by the Quechee Gorge.  While we didn’t do the full hike, we walked around a bit and of course snapped a few pictures.

The kids also loved the souvenirs at the little shop.  They had the best selection of keychains, magnets, and water bottle stickers of anywhere we visited in Vermont!


Travel tip with kids: Allot them a certain amount ot their sounvenir money per day or per attraction!  Our kids decided to try and get a keychain in each state we visited.  Perfect because they can use them on the backpacks and they are budget-friendly, fun reminders of the places we stopped!


Vermont Antique Mall, Quechee, Vermont

Of course, we made an impromptu stop!

You didn’t actually think we’d drive past a place this cute without stopping, did you?!  Robb and the kids grabbed some maple sugar snacks and toured the toy museum.

They set the timer for me to make a quick stroll this this antique mall.  What a great stop!

I needed a lot more time and a much larger suitcase!

I had to leave behind this incredible antique French basket because it was too wide for our suitcase (yes, we actually measured because I loved it so much!).

I did pick up this cute set of bells for a great price and they will be especially fun to style in our Christmas decor each year.

Taftsville Covered Bridge, Woodstock, Vermont

There are four picturesque covered bridges around Woodstock!

Of course, at the first sighting of a covered bridge, we pulled over for a few quick pictures.  And we weren’t the only ones!  There was a steady line of cars pulling through to take pictures of this sweet place!

We only stopped and took pictures by two of the covered bridges, but if we ever go back, we know we need at least two days around this beautiful town!

Sugarbush Farm in Woodstock, Vermont

Perfect family fun and delicious too!

Sugarbush Farm was a favorite stop for all of us!  It was a great place to spend a couple of hours, have a great Vermont-style experience, and learn a little bit too!

We started off with enjoying samples of cheese and 4 different flavors of maple syrup, all made right there on the family farm.  The Sugarbush Farm is a multi-generational operation and truly a family business.

I knew next to nothing about the maple syrup process and my kids definitely didn’t either!  The lady was so nice to explain the different colors of syrup and how they change based on what point in the season the syrup was collected!

Next, we took a walk through the woods, following the sap lines and reading the information posted about the syrup process.  I loved learning that they still use horses and sleighs for part of the gathering!

The kids got to try their hand at carrying a bucket with the weight of the syrup and trudge through the uneven snow (simulated with the tires).  They all decided that the sap line was a great invention!

We visited the adorable little chapel on Sugarbush Farm and watched a video presentation about the ins and outs of the family business!  I have a much greater appreciation for delicious maple syrup when I use it on my waffles!

We enjoyed snapping a few more pictures of the gorgeous scenery and of course, left with some souvenirs!  We brought some syrup and cheese back to Florida with us!  Yum!

Picture Perfect Town of Woodstock, Vermont

We see why it’s been called the most beautiful town in America!

We enjoyed strolling the downtown streets and stopping in at the unique shops.  The kids loved the bookshop and I loved seeing all the fall displays and window boxes!

Of course, we had to get ice cream!  Woodstock Scoops has the BEST homemade ice cream and maple sugar sprinkles. Yum!  I’m still kicking myself for not purchasing sprinkles to bring home!

We also scheduled a photographer and had a mini-photo shoot by the covered bridge in downtown Woodstock, Vermont.  You’ll have to wait until our Christmas card is ready, but here is a quick snapshot I took while the photographer was getting ready!

Have I mentioned that Woodstock, Vermont is the most picturesque little town?!  Every corner is a photography opportunity.  I finally just had to stop myself and remember to enjoy the moment!

Woodstock, Vermont also had a dream for sale.  Look at this old pharmacy building, original signs still there, just waiting for a loving owner!  I hope to visit again and I hope someone turns this into the cutest shop on the street!  It had me dreaming for a few minutes, I’m not going to lie!

Woodstock, Vermont…you were so kind to our family!  What a beautiful day, full of moments that I will keep tucked in my heart.  While I felt blessed to be strolling the streets of what looks like a Hallmark movie, I felt most blessed to enjoy it with the people I love the very most!

Woodstock, Vermont…you were so kind to our family!  What a beautiful day, full of moments that I will keep tucked in my heart.  While I felt blessed to be strolling the streets of what looks like a Hallmark movie, I felt most blessed to enjoy it with the people I love the very most!

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