A Weekend Away in Vermont: A 4 Day Itinerary

We just got back from a weekend away in Vermont, and just like every time we head up to the Green Mountain State, we never want to leave. Every time we go up for a long weekend, we seem to want to extend our trip longer and longer. The end of this trip was marked by several weeks of real estate hunting accompanied by the beer and cheese we brought back with us. We really like it more and more each time we go.

And why do we love Vermont so much? The maple syrup? The beer? The cheese? The people? The views? The nature? The architecture? The flannel? Yes to all of the above. Vermont is no one trick pony.

Boston, New Haven, New York, Albany – all within easy driving distance. But when you cross into Vermont, it feels like you’re worlds away. The rolling hills and winding roads open ahead of you. As you drive into the state, you can finally unclench that steering wheel and enjoy the ride. The white knuckle-driving from the NJ Parkway and I-95 are a thing of the past now.

It is truly peaceful up here. The dark at night is actually dark, but a grocery store and “town” are also not too far away.

The “love what you have” attitude favors rehabilitated buildings over extensive new development. And let’s not forget the ridiculously quaint small towns you drive through. Each one the same concept – main intersection with a general store and some antique shops or art studios – but each one with their own charm and personality.

And of course – THE LEAVES. We all know the cliché autumn image that appears on social media every year – a photo taken from a higher vantage point looking out over the landscape of saturated reds, yellows, and oranges. Maybe throw an old church or barn in there, too.

But being there during the fall time really is something else. That beauty of the leaves and mountains is captivating and something that cannot be captured with a picture.

Also, the impressive craft beer and cheese industries that thrive in Vermont are reason enough to make the trip. Our trunk was full of beers, cheeses, oh and maple syrup. I think we bought more maple syrup on this trip than we have ever eaten combined.

Ok have I convinced you to take the trip? Time for some trip planning.

On this last trip, we did a 4-day long weekend. Where we went was a 7-hour drive from our New Jersey home, and 4 days provided a good amount of time for driving and relaxing. Would be have liked to do longer? Of course. 5 days would have been perfect for our beer and cheese-focused trip with a big emphasis on sleep and relaxation.

Our 4-Day Itinerary for a Weekend Away in Vermont

Day 1 Thursday

Day 1 on our trip was the drive up. There was unfortunately an incredible amount of traffic for a Thursday morning. If you’ve ever driven on the New Jersey Garden State Parkway anywhere north of Exit 140 (yes, we do sometimes identify our location by exit numbers), you know the frustration of traffic on this narrow and windy stretch of the highway where everyone seems to have lost all sense and forgotten how to drive.

(Why do we love Vermont? They seem to all understand how to drive).

Our final destination, Greensboro, is over 7 hours from our New Jersey home. So we broke up the drive into several fun stops.

Pizza and Frank Pepe Pizzeria Napoletana, New Haven, Connecticut

We made it to our first stop, which was lunch at Frank Pepe Pizzeria Napoletana in New Haven. This wasn’t exactly a planned stop, but we knew we would need lunch and some friends of ours had recently visited New Haven. This famous and timeless restaurant was number 1 on their list of pizza places in New Haven. And lucky for us it was very close to the highway exit so an easy stop.

Frank Pepe’s is famous for their clam pizza. So obviously we partook in this (apparently) time honored tradition. We also got a sausage and peppers pizza in case the clam wasn’t our jam. At the recommendation of our waitress, we added bacon to the clam pizza, which turned out to be a wise choice.

The clams and bacon worked – we thorough enjoyed this strange combination. Although truth be told I probably don’t need to eat it again. It was an A+ stop.

Beer at Tree House Brewing Company, Deerfield, Massachusetts

We moved on another hour and a half north to our next stop at Tree House Brewing Company in Deerfield, Massachusetts.

We have been to a Tree House Brewing location before (John has been to several), but this one was new for both of us. After picking up our pre-ordered personal warehouse of beer, we headed over to their tasting room.

The facility is an old office complex built in the 1970s. I know what you’re thinking – a 1970s office building doesn’t exactly say “cool modern brewery,” but it very much was a cool modern brewery. Not only is the tasting room in the “winter garden,” i.e., big beautiful greenhouse, but there is a huge outdoor area to sit and lots of walking paths around the property.

If only I liked IPAs…

Still had a great time here – and the weather couldn’t have been more perfect.

Sight Seeing at Quechee Gorge Bridge, Hartford, Vermont

From here we continued another hour and a half or so to the Quechee Gorge Bridge in Hartford, Vermont. The bridge was built in 1911 and is on the National Register of Historic Places. You can hike down to the water to view the bridge from beneath or go up toward the dam at the southern end.

We got there a little late and were losing the sun. We also thought the walk down would get us a little closer to the bridge and it did not. It was still a good little walk there and back.

Cocktails and Dinner, Montpelier, Vermont

Our next stop on our drive north was Montpelier, this state’s fine capital. We love this little Vermont city – it has the quaint small-town New England feel with great food and art. Lots of locally owned stores here that are great to peruse at leisure.

Our predetermined destination was Caledonia Spirits Distillery, home of Barr Hill Gin, a gin that we’ve used over and over in some of our favorite cocktails (hello, Bees Knees). What do you get when you combine a lifelong bee keeper with an expert distiller? Some truly wonderful and special spirits.

In 2019 they moved from their original home in Hardwick, Vermont to their current place of business on the aptly named Gin Lane in Montpelier.

We sat inside at the bar and enjoyed some perfectly mixed and delightfully tasteful cocktails as well as our first cheese plate of the trip.

While we were enjoying our drinks and cheese, we took a look through Google to find where we wanted to eat dinner. Kismet on Barre Street stood out to us. Luckily on a Thursday night they didn’t seem too busy so we made reservations online for later that night.

A small, farm to table restaurant, Kismet offers an intimate setting (probably about 20-ish seats in there) and a great variety of dishes. There was also a musical trio playing when we got there, which set the mood perfectly.

Greensboro, Vermont

Our Airbnb was about a 50 minute drive from Montpelier. We stayed in Greensboro, in a little cabin just outside town. It was about 10:30 pm by the time we arrived and we were definitely exhausted. We got settled in, then fell right asleep.

Day 2 Friday

Breakfast and Hiking

We slept in (ahhh) and completely took our time in the morning. We went down to the general store, The Willey’s Store, to get some coffee and stumbled upon some delicious locally made donuts. Of course couldn’t resist.

Back up at the house, we enjoyed our coffee and donuts in some Adirondack chairs on the deck. A very civilized way to begin a day.

We both had a bit of a cold and so weren’t up for a big hike on this trip. Plus we had slept way too late to head out to any of the better trails. Instead we drove a few minutes over to the Barr Hill Natural Area and did the quick loop trail that still offered some pretty amazing views and foliage.

Beer at Hill Farmstead Brewery, Greensboro, Vermont

Hill Farmstead Brewery was one of the first places we went together when we started dating, and we have been back a couple times since. This is the first time we were there in warm enough weather to sit outside.

John made us reservations (which they do seem to prefer although walk-ins are welcome) for 3:00. Only a 6 minute drive from our Airbnb, this was a great way to spend the second half of the afternoon.

Even though I am not a beer enthusiast, I can tell their beers are something special. I always enjoy what I have from there and can completely understand why they are so sought after.

We had pre-ordered some cans and bottles so we picked those up first, then enjoyed several beers and another cheese plate in the lawn. The weather was also absolutely perfect.

Dinner at Blackbird Bistro, Craftsbury, Vermont

As the sun started to set, and the temperature went down, we decided it was time to head on from Hill Farmstead. Because of our delicious cheese platter, we weren’t quite ready for dinner yet so we played a few card games at our Airbnb.

As a side, we love to take easy-to-pack games on our trips for when we have these times in between activities or just want some downtime. This time we brought Gloom with us, a delightfully dark and silly card game with some very Edward Gorey-esque artwork.

We ate dinner at Blackbird Bistro in Craftsbury, about a 15 minute drive from our Airbnb. They don’t take reservations so we put our name in and waited by one of the firepits, as it was now quite cold outside. The bar was opened so we enjoyed our cocktails while I pretended like I hadn’t chosen the wrong footwear.

We ultimately sat at the bar, our favorite place to sit at any restaurant, and ordered wings and burgers. It look over an hour for our food to come and then it all came out at once. We got the idea this is just how it is there, but oof we were hungry by then. It was all very good and everyone there was very friendly.

When we leaving we heard one of the waiters say to another “you’re always the best when you’re the only option in town.” Which is totally true. Your options are limited. Always good to remember to be flexible and understanding with your waitstaff!

Day 3 Saturday

Russian Honey Cake

Day 3 started as Day 2 had – a trip to the Willey’s Store to get some coffee and back to the house to enjoy it on the deck. We didn’t get donuts this time though. When we were at Caledonia Spirits, we purchased a Russian Honey Cake from a local baker, owner of Matryoshka’s Bakery, who had set up a table selling her pastries.

We decided to eat it for breakfast Saturday morning. It is absolutely impossible to describe how delicious this Russian Honey Cake was.

And what is a Russian Honey Cake, you ask? We had never heard of it before, either. Originating in Imperial Russia and seemingly becoming popular during the Soviet era, a Russian Honey Cake, or Medovik, is a layered sponge cake made of honey and smetana (sour cream) or condensed milk.

There seem to be many different variations on this pastry, and after splitting this small cake, we wished we had bought more!

Cabot Farmer’s Store and Smugglers’ Notch Distillery, Waterbury Center, Vermont

Our plan for Saturday was to head out to Burlington. We realized on our drive that the Cabot Farmer’s Store was right along the road that took us to Burlington (Rt 100) . So we decided to take a unscheduled stop for some cheese.

This is probably one of the more touristy cheese stops in Vermont, but I love a good Cabot cheese, and in their store there are samples everywhere. They also had a lot of jellies, jams, and honey. We tasted a lot of jellies and jams that were paired with Cabot cheeses.

We bought ourselves an awesome Jalapeno & Lime jam from Blake Hill Preserves.

On the same property is the Smugglers’ Notch Distillery. They partner with a local maple sugaring operation, which goes into creating not only a Maple Gin, but also a Vermont Maple Cream Liqueur, which was sinfully good.

We each did a tasting of 4 of their spirits. We then noticed a large barrel with bottles of maple sugar sitting on top. Yep – they make barrel aged maple syrup, aged in their used bourbon, rum, and rye barrels. So we got to sip a little cup of some excellent maple syrup.

And so we left here with cheese, jam, Maple Cream Liqueur, small gins and ryes, and some maple syrup.

Church Street Marketplace, Burlington, Vermont

After our fun food purchases, we were onto our last leg of the drive to Burlington. Without our cheese and spirit stop, Burlington is an hour an a half from Greensboro. While not the capital of Vermont, Burlington is the largest city and is home to both Champlain College and the University of Vermont.

Like all good college towns, Burlington is rich with history, culture, and art. Burlington was also the first city in the country to meet 100% of its residential electricity needs through renewable energy.

We didn’t have a formal plan for our afternoon in Burlington. Just wanted to walk around and check out the city. We parked in a municipal lot (there are a lot of these – we found it very easy to park) and headed over to the southern tip of Church Street. The Church Street Marketplace is a four-block-long pedestrian street consisting of shopping, dining, flannels, and street performers on every side.

The Church Street concept dates to 1962, but it wasn’t ultimately constructed until the early 80’s. As city planners we are in love with this pedestrian-focused downtown experience.

Church Street is a great place to grab a snack from a street vendor (John chose some rich poutine) and soak in the sun while people watching. The stores are a mix of national chains and local businesses. We squeezed our way into the tiny Vermont Flannel Company store and purchased some very cozy flannel. I mean, how could we not.

Foam Brewers and Creemees, Burlington, Vermont

After successfully walking up and down Church Street twice, we headed over toward the waterfront. It was a very easy and short few minute walk from Church Street to reach the water. We stopped at Foam Brewers for some beers and yes, another cheese plate. There were a lot of very interesting beers here that included both hoppy and other. The weather was great so we enjoyed ourselves outside at their rear dining area.

This cheese plate had some of our favorite cheeses of the whole trip, and we were kicking ourselves for not asking what they were. But they were all delicious.

After a few rounds, we gave up our seats to one of the many groups waiting (it was a beautiful and busy Saturday afternoon), and walked the short but beautiful waterfront walkway. At the end was an ice cream truck selling a Vermont staple – the Vermont Creemee. A creemee (yes that is how it’s spelled) is a soft-served ice cream but definitely don’t call it that. And the true pinnacle of the creemee is the maple creemee.

Combining two of the things Vermont is most known for (dairy and maple syrup) creates one of the most delicious treats to enjoy on any afternoon.

Freak Folk Bier, Waterbury, Vermont

On our way back toward our Airbnb and dinner, we stopped at one more brewery, Freak Folk Bier, in Waterbury. The small brewery is tucked almost under the Stowe Street bridge. The beers here are earthy and easy to drink. The sun was setting, as was the temperature, but we cuddled up on a bench in their small front yard and enjoyed our second to last stop of the day.

Dinner at The Parker Pie Company, West Glover, Vermont

Our last dinner in Vermont was at The Parker Pie Company in West Glover. We were about half an hour from the Canadian border at this point. As we mentioned earlier, restaurants out here are few and far between. We stumbled on The Parker Pie Company while searching for places to eat when planning our trip, and it did not disappoint.

This local pizza place is in the back of the Lake Parker Country Store, and offers local Vermont beers and delicious pizza. Just like our experience at Blackbird Bistro, our pizza took about an hour to come out. But we were in no rush, and thoroughly enjoyed the guitar player while we waited.

For anyone who decides to come out here – it is absolutely worth it as the pizza was fantastic. Just remember you are in farm country, and the cows are close by. So don’t be alarmed by the occasional essence of cow that may waft its way over across the road.

A 25-minute drive south brought us back to our cozy cabin to end the night.

Day 4 Sunday

Drive Back Plus a Stop at OEC Brewing, Oxford, Connecticut

We enjoyed our last morning in Greensboro with some more local coffee and donuts on the porch before packing everything up to head back to New Jersey. We would have loved to spend one more day up here but real life was calling.

It was another gorgeous day so we enjoyed the views as we headed back south.

We made a stop at OEC Brewing in Oxford, Connecticut to break up the trip a little. And of course had to get a pretzel and one more cheese plate. We liked the beers here but were pretty tired and anxious to get home. So we each enjoyed one beer and were on our way.

Weekend in Vermont Summary

We definitely recommend a long weekend away in Vermont. In just a few hours’ drive you’ve entered into a completely different world. Their famous dairy, maple, and beer drew us to Vermont this time, but there is so much to do and many more places to visit than we had time for. We came home with more beer and maple syrup than we really know what to do with (well, we KNOW what to do with it) and we will absolutely be back soon.

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