Peep Those Leaves: A Weekend in Vermont

leaves weekend vermont


Is there anything more quintessentially fall than September through November in New England? If there is, you’re going to have to tell me about it, because I need to know. In my mind, nothing says fall like a landscape of leaves ranging from red to orange to yellow – well, except maybe cider and sweaters. My friend Sally and I decided that spending a weekend in Vermont to see all the leaves would be just the perfect getaway to celebrate a new season – and Vermont, you did not disappoint!


If you’re looking for a great weekend road trip, I’d highly recommend checking out the East Coast – so many great little towns full of #Americana. Thinking of going? Here’s what we did and loved!


Where to Stay

Peep Those Leaves: A Weekend in Vermont - our Airbnb studio

The stairs led up to our private Airbnb studio.


We were pretty intent on staying in an Airbnb while in Vermont – during this time of year, hotels and bed and breakfasts can get pretty pricey and we wanted as unique of an experience as possible. We looked at a lot of different properties – farms, apartments up in skiing towns, even tiny houses and a yurt (seriously!). In the end, we found a perfect studio apartment in Strafford that looked to have amazing views at a great price. The location is kind of crazy – no cell service and definitely rural! – BUT I would highly recommend staying with Barbara and Wally. They were so accommodating, the studio was exactly what they needed, and they stocked the fridge with fresh maple syrup and apple butter their son had made. Plus, the wrote a book on bicycling through Cuba that is apparently really popular, and they get visitors from all over the world because of it! You can read my review on their profile for more details : ) [pssst…first time Airbnb user? Use this link for $40 off your first trip!]


What To Do

We decided that we wanted to see as much of the state as possible, so we hopped from city to city instead of just staying in one place. Plus, isn’t part of the trip driving through the state and taking the scenic route to see all the beautiful colors?




Peep Those Leaves: A Weekend in Vermont - Woodstock

Our first stop after the drive over from Boston Logan was in Woodstock. I had read that it was a picturesque little town with lots of little shops and good photo opps – perfect, exactly what we were looking for! Every house is adorable and just looks so stately and colonial. There is a great covered bridge with trees in the background (there’s your photo opp). The shops were really fun to look through, and ranged from pretty upscale boutiques (they target the skiers during the winter) to sporting stores to local are to, you guessed it, FLANNEL.


Peep Those Leaves: A Weekend in Vermont - Quechee

Standing on the bridge over the Gorge – the sun was doing some cool things!


After grabbing some baked goods and coffee, we drove over to see the Quechee Gorge (technically in Hartford, VT). Seeing the bridge was absolutely stunning. We decided to walk the bridge to take some pictures, but we also took the Quechee Gorge Trail to be a little more “in it.” Don’t worry – it’s not a serious hike by any means…just a nice little path in the woods that leads you under the bridge and to a dam. These were some of the best sights and pictures of our trip!


Peep Those Leaves: A Weekend in Vermont - Sugarbush

Learning how to carry a “bucket full of maple syrup” (read: rocks) through the “snow” (read: tire obstacles).


For our last adventure of our first day, we circled back a bit to hit up Sugarbush Farm in Woodstock. This little farm is really interesting. They offer a lot of different experiences – none of which are high tech or overly developed in any way…and that’s what gives it its charm! The little farm has a cheese packing room where they let you try their various assortment of cheeses (free cheese tasting? Yes please!). There is a shop that has more tastings – jams and spreads and syrup and the like. A small old barn takes you through the process of tapping a maple tree and processing the syrup. This is then accompanied by something called a “maple walk,” which is really just a few numbers to follow on their property to give you a sense of what it’s like to gather the sap and how much is needed to make syrup. There’s a tiny old church house on the property as well. It’s semi-creepy because it feels stuck in the distant past, but definitely interesting to see the little photobook of people who have gotten married there (and apparently it’s not just their family members?!). Finally, they have some animals right when you drive up that are fun to look at and pet…and who doesn’t love that. What’s more, the landscape is gorgeous. If you’re looking for sweeping views of the countryside, this would be a great place to find it.


Stowe + Burlington

Day 2 for us was a lot of driving – we made it to the top of the state and back, stopping at points of interest all along the way. To be fair, both Stowe and Burlington could likely have their own sections. However, we didn’t spend too much time in Stowe, so I decided to include them all in one.


Peep Those Leaves: A Weekend in Vermont - cider donuts



Stop 1 for the day: Cold Hollow Cider Mill. All the apples. All the cider. All the cider donuts. Need I say more? Probably not. All you need to know is that this shop has tons of legit souvenirs, should you need something to take home, and delicious hot cider donuts that will start your morning off right!


Peep Those Leaves: A Weekend in Vermont - Ben and Jerry's

Ah, the Mini Vermonster – look at those toppings!


Because cider donuts weren’t enough sugar to start our day off with (eye roll), our next foodie point of interest was Ben and Jerry’s Factory in Waterbury, VT (on the way up to Stowe and Burlington). The tour of the factory was awesome – the tour guides are super fun and knowledgeable, and it was great to learn more about how the company is intent on doing good. Plus, free ice cream at the end. #PTL. However, what we really came here for was the Mini Vermonster. The Original Vermonster is a behemoth that comes in a plastic bucket…we’re talking 20 scoops of ice cream, with a few cookies and brownies and any topping you can imagine thrown in for good measure. Since we’re responsible, we shared the mini version…how could you honestly pass that up? #wheninVermont. Sadly, we still couldn’t finish. Worth a try, though!


Peep Those Leaves: A Weekend in Vermont - Church Street

The view down Church Street Marketplace.


We drove through the town of Stowe, but outside of a few boutiques, didn’t find much. Could be because it wasn’t skiing season? Or maybe we did it wrong…I don’t know : ) That said, we stopped by a tasting at Smuggler’s Notch Distillery to try some of the local liquors – and our bartender was from Indiana! Go figure.


Once we finally made it up to Burlington, we had a blast. As we drove into town, we could see Lake Champlain at what felt like the end of the street, so we followed the road down to the marina / lakeside to catch a closer look. Then, we spent the rest of the afternoon walking up and down Church Street Marketplace and stopping in stores before heading back to the studio (it gets dark so early!). We both really liked the vibe of Burlington – Sally said it reminded her of Portland – and I can imagine there is so much more to explore around here if you have more than a day.


What to Eat

Peep Those Leaves: A Weekend in Vermont - what to eat

NY Strip Steak + mashed potatoes + the best vegetables I’ve ever eaten from Stone Soup Restaurant


Okay, to be honest, when we asked around to our friends who live in Vermont what we should do, pretty much every recommendation revolved around food. Which we were more than okay with! I mean, come on. From the locals themselves, when you go to Vermont, here are the things you need to make sure you eat:


Apple cider donuts + hot apple cider: There are dozens of places to find these goodies. We had multiple throughout the trip, but our favorites were from Cold Hollow Cider Mill.


Ben and Jerry’s Factory: Two words: Mini. Vermonster. Also, how are you trying to pass up free ice cream!?

Fresh maple syrup: it’s everywhere.

CHEESE!!!: it’s also everywhere.

Hard cider: You’ll find quite a few hard cider brands in the land of many apples. I wasn’t able to try Stowe Cider (they were closed when we passed through), but I got some Citizen Cider and really enjoyed it.


Heady Topper by The Alchemist (Stowe): This brewery is a Vermont original that canNOT be found throughout the US. Hence, when people are in town, it’s a big deal to pull over and grab a cooler full of their famous Heady Topper. Lines start pretty early, so if you want to go, it was recommended to us to get there a bit before opening time. I don’t really like beer, so I can’t comment on the flavor…but Sally liked it, and they had a cool showroom. If nothing else, they have great branding


Finally, Stone Soup Restaurant: There is no way you would just accidentally run into this place. You probably would have a hard time finding it online unless you were searching for it by name, too. This restaurant is absolutely amazing, though…could it be one of Vermont’s best kept secrets?! Stone Soup was listed as a recommendation in Barbara and Wally’s welcome book…and you guys, that dinner was one of the best meals I’ve ever eaten. The food was so so fresh and expertly prepared. I can’t recommend it enough! However, be sure you have enough cash to cover the bill – it is a cash-only restaurant. We didn’t know and got a few confused looks when we laid our cards down. We didn’t have enough cash on us (it’s a bit pricey)…so all we could do at that point was write down the phone number, give them my email address, and promise to be back the next day to pay. Luckily, they were understanding and didn’t make us stay to do dishes to earn our dinner ; )


A Few Other Things You Need To Know…

Peep those Leaves: A Weekend in Vermont - SolMates socks and hard cider

Relaxing with some cider and my SolMates!


  • I would recommend going in the first or second week of October to see the most vibrant leaves. Although I’ve heard that there’s no perfect time to go, the leaves start to change around mid-September. We went during the first week of November, and unfortunately, it rained the day before we arrived, knocking most of the leaves off the trees. We still saw some beautiful colors, but had we gone a week earlier, it would have been an entirely different view!
  • There are some verrrrrry rural areas of VT. To make sure you don’t get lost in the backroads – where cell service is super spotty – make sure to pre-plan your route and take screenshots of the map. There were more than a few times where we couldn’t “find our dot” on our phones, so those screenshots were a lifesaver to remember the names of roads and where to turn. Barbara and Wally did not have cell service either, so if that’s an issue, definitely check the Airbnb listing to make sure your host has service. (The yurt didn’t – haha).
  • Grab a pair of SolMates socks! This is the one thing I came back with, besides a great mug. The socks are fun colors in a warm and cozy knit, and the pair is mis-matched so the two socks are different. I got the knee high Poinsettia color (deep maroon and forest green) because they go with my fall/winter wardrobe. They are great scrunched down with boots!


And there you have it – our rundown of everything we experienced in about 48 hours in Vermont. Have you visited any of the cities we mentioned? What did we miss?


Peep those Leaves: A Weekend in Vermont





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