Until my recent weekend in Vermont, I had visited all the New England states but one. That’s basically like living in your house for five years and never going into the attic. Who knows what’s up there? Overflowing maple syrup? Tons of flannel? Hippies? Actually, yes, all of the above.
I’m talking about Vermont—land of, well, maple syrup and flannel, but also craft beer and marijuana as decorative house plants. Home of Ben, Jerry, Phish, and laws that prohibit billboards. And the last of the New England states to be scratched off my map.
The most popular cities in Vermont are just a few hours’ drive from Boston but the whole state seems a WORLD away.
Burlington (3.5 hours) is a town that prides itself on being wEiRd, much like Austin, TX and Portland, OR—I mean, it boasts the world’s tallest filing cabinet. Do with that what you wish.
Stowe (3 hours) is the closest you can get to the Austrian Alps without being frisked by TSA security. Signs are written in French and there are constant reminders to beware the moose and bears. Where are we?
What I’m trying to say is, a weekend in Vermont is the perfect getaway. It’s got everything a relaxing vacation should have: the great outdoors at your fingertips, local shopping, eating, and drinking, covered bridges, leaf peeping, someone playing James Taylor on a guitar in the corner, virtually zero contact with the outside world, and, okay fine, decriminalized weed.
1. Stay at an awesome vacation rental
Vermont is the perfect place to rent a vacation home—you can be as secluded and distanced as you want to be. Check out these awesome Vermont vacation rentals for your weekend in Vermont!
Lovely Treehouse in the Woods
You’ll have this entire treehouse to yourself and it couldn’t be cuter. It has a deck, sitting area, hammock, campfire space, and is totally environmentally conscious.
Book your stay: Vermont treehouse in the woods
Barn and Silo home
For larger groups (sleeps up to 10), this full-sized barn with silo makes a super fun and unique weekend in Vermont! Located near Stowe, this place is in a great location for hiking, skiing, beer drinking, and more.
Book your stay: Barn & Silo home
2. Grab a meal at the Wayside Diner
Just outside Montpelier, just off the highway, is the historic Wayside Diner—home of “home cooking away from home.” Y’all, I told you Vermont was CUU-UUTE.
The Wayside Diner serves breakfast, lunch, and dinner, and the food is DELICIOUS. They serve fresh, local, in-season ingredients in an adorable down-home environment that provides that homesick for the South fix I need every now and then (without all the decorative pillows and horse sweaters that clog up the entrance into Cracker Barrel).
They were named Montpelier’s first and only Green Restaurant for their significant contribution to environmental sustainability—they use solar panels to heat the water, they compost, they utilize efficient transportation, and work closely with local farmers and fishermen.
They’ve gotten rave reviews from the New York Times, the Disney Vacation Guide, and Gourmet magazine, as well as awards for sustainability and soon enough they’ll have an Emmy if I have anything to do with it.
3. Burlington Farmer’s Market
After your bed and your breakfast and your putting on flannel, head over to Burlington and start your day at the Burlington Farmer’s Market—every Saturday from 8:30 until 2:00 (10 – 2 in the winter).
And, well, it’s a farmer’s market so there’s not a whole lot I can say. But it’s also Vermont so I’m going to say MAPLE SYRUP and locally grown organic produce and mountain-centric arts and crafts, live music, friendly puppies to pet, vintage clothing, tons of delicious food vendors, and actually loads of booze surprisingly (but also unsurprisingly). They even had whiskey and vodka distilled from maple syrup so if that’s a thing you need in your life, here ya go.
Their website even has a chart of what is in season and when so you can shop accordingly. Vermont, you’re adorable!
4. Check out Church Street
In downtown Burlington you’ll find hip Church Street and the flannel shops that adorn it. You’ll find boutique eateries, outdoor supply companies, hip local shops mixed with hip national chains, and a one-man band with an accordion and bells on his legs. (Maybe we should rethink that *legal weed* thing?)
Church Street dates back to 1962 when an architecture student saw how the model of pedestrian-only malls worked in Copenhagen. Today, it’s a great place to day drink in the sun, people watch, and enjoy unique events like the Vermont Fire Truck Pull, the Festival of Fools, and trying not to make eye contact with the guy with the accordion while at the same time really appreciating his rendition of that song from that thing!
(OK, Vermont is too stinkin’ cute—they’ve got a page dedicated to the bios of their street performers. I mean really.)
5. Visit the Ethan Allen Homestead
Ten minutes from Church Street is the Ethan Allen Homestead Museum where you can learn about life on the Vermont frontier and all about the life and legacy of Ethan Allen, Revolutionary leader who has absolutely nothing to do with home décor.
Your pretty-much-private tour will teach you how to make linen from plants, mattresses from ducks, and lemons into lemonade given that you’re basically just postponing your beer drinking at this point and that’s a little more adversity than you were hoping for your Saturday.
The museum is located on the property of Ethan Allen’s final home which still stands and where most of the tour takes place. So if you want to squeeze in a little bit of historical education into your trip so it’s not completely about getting schnozzed in the mountains, this is your stop. If you were hoping to snag interior design pointers, move along…
6. Craft beer time
Did you know… Vermont is the craft beer capital of the United States? It’s so called because there are more craft breweries per capita in Vermont than any other state. That’s 11.5 craft breweries per every 100,000 people actually—which means there are like a million craft breweries in the tiny state of Vermont. And what that means is that a single weekend in Vermont is just not gon’ cut it! WHAT WERE WE THINKING!?
Stone Corral Brewery
Fiddlehead Brewing Company
Fiddlehead Brewing Company is Known for their flagship IPA and disliked by Ashley because they don’t serve flights!? You mean I have to drink a regular-sized beer? Psshh! Anyway, they also have a pizza restaurant attached and are located across the street from a winery in case your group needs to split in half. Beer to try: Betty Nelson Raspberry Wheat (What? I don’t like hops, shut up.)
Magic Hat Brewing Company
Magic Hat Brewing Company is the most *mainstream* of Vermont’s craft breweries but also the most *WTF is going on here fever dream* of them all.
The brewery tour here is very, very wEirD but you get to see the entire working beer factory, sample four different beers, and experience what it would be like if Willy Wonka’s factory tour actually took place inside a Jerry Garcia acid trip. Beer to try: Magic Hat #9
Update: Magic Hat has permanently closed their Vermont brewery.
Zero Gravity Craft Brewery
Zero Gravity Craft Brewery has great lagers, popcorn, an awesome patio, and I met a couple from Tennessee who I became instant BFFs with, obvs. (Hey, y’all!) My favorite brewery of the day, and a favorite of the locals I learned. Beer to try: Zero Gravity Oktoberfest—but like, hurry!
Queen City Brewery
Queen City Brewery is right across the street from Zero Gravity, also has a pizza place attached that you should totally order from (get the Go Ask Alice) and Q-shaped pretzels. Beer to try: South End Lager—I’ve been drinking for hours, it’s time to lighten things up.
Switchback Brewing Company
Switchback Brewing Company has, not gonna lie, I don’t even remember what I had here. This was brewery #5 of the day and at that point beer was beer. I remember the service was great! And lots of bright colors. And a giant fish outside… hmm… Beer to try: Yes, try the beer!
And Von Trapp Brewery because drinking beer is one of my favorite things… this brewery gets its own section in this post! Read on.
7. Eat lunch at The Spot
Burlington, Vermont is not short on adorable (and probably delicious) places to eat but let me recommend to you: The Spot. The Spot is, randomly, a surf-style restaurant in a repurposed 1950’s gas station. Because why not! This is the “west coast” of New England, after all.
The food is delicious, the portions are huge, and the atmosphere is TOTALLY GNARLY DUUUDE. They have surf boards and a fish tank and, of course, boast fresh, local ingredients, wind and solar power, and attention to plastic-free detail. Cowa-freaking-bunga!
8. Check out cute local shops
So yeah, you’ve heard me say Vermont is cute like a hundred times. So this’ll be 101. In keeping with the Hallmark movie tradition here, you must visit some of the cute local shops during your weekend in Vermont.
For starters, you’ll want to pick up some flannel lest you stand out like a person in Vermont who’s not wearing flannel. Hello, tourist alert! Put on your flannel and head into a general store for various gift items, Vermont things, and everything maple.
Follow your lunch with a maple creemee and ride that sugar high like Pipeline. (Vermont’s version of maple-flavored soft serve ice cream, the marriage of the state’s two most prolific industries. I told you this place was dripping in quirky romance!)
Flying Pig Bookstore
From there, check out the Flying Pig Bookstore. They’ve got more than 30,000 books, each carefully picked, and the place is covered in color, helpful book descriptions, unique cards and gift items, and just an overall hip aura.
And this is just the start of it. If you haven’t picked up on it yet, Vermont is all about the hip and local. Avoid the national chains during your weekend in Vermont and support local businesses! They really are the most precious.
9. Go hiking in the Green Mountains
Okay so the reason most people spend a weekend in Vermont in the fall? Those leaves, baby! You know… #fallvibes, #sweaterweather, #leafingsummerbehind? And the best way to see them is on a hike through the Green Mountains. << How about that irony?
Admittedly, I visited shortly before proper leaf peeping season began, but the experience was no less aWeSoMe. We chose to hike Mount Mansfield because it’s the tallest peak in Vermont–but also because it’s so named because it “resembles a man’s face” and we got to hike “the Chin.” Eat your heart out, Gulliver!
This hike is perfect for a weekend in Vermont because:
- It’s only about 2 hours round trip (nothing like the day-long hikes in Chamonix)
- You get all the hiking views and experience without all the work
- It smells amazing (Is this not how you rate your hikes?)
How to get to Mount Mansfield
For this short hike, you’ll drive up the mountain most of the way, hike to the summit and back, and drive back down. Call it cheating if you want, but I prefer to call it “the only way I can fit a hike into only a short weekend in Vermont.” Potato, potato. Dammit this should’ve been a podcast.
How to hike Mount Mansfield
To hike Mt. Mansfield, first ascend the Auto Toll Road at Stowe Mountain Resort–a 4.5-mile mountainside drive full of leaves to peep and incredible views (so I’ve heard). Drive until you can’t anymore and park next to the information center. Go inside to learn about local Alpine flora and fauna and to ask the parks employee about your chances of being chased by a moose (unfortunately, zero).
The start of the hike is right there and the hike to the summit could NOT be easier to follow. It’s the most well-marked trail I’ve ever hiked and the strings intended to keep you off the plant life in turn keep you on the trail. If I could do it in total whiteout conditions and super strong winds without getting lost, anyone can! I mean it, even Ikea is harder to navigate.
What to expect on the Chin Hike
The Chin hike to the summit of Mt. Mansfield is incredibly interesting. There are no wild animals to worry about but the trail is abundant in awesome-smelling fresh pine, rare Alpine flowers, and, supposedly, offers unbelievable views of Vermont and all the way to Canada. (The Green Mountain Club guide at the summit told us on a clear day you can see the Montreal skyline!)
The hike is more of a climb than a hike with more rock scrambles than hiking paths so be prepared to use your hands as well as your feet. Even in terrible weather conditions and absolutely zero views, this hike was still the highlight of my weekend in Vermont.
10. Visit the Von Trapp Bierhall & Family Lodge
Next up is a visit to the von Trapp brewery, bierhall, and family lodge–or, what I like to call The Sound of Music 2: WTF happened after they fled the Nazis?
Well, I’ll tell ya. After fleeing Salzburg, Austria in 1938, the von Trapp family toured around the world as the Trapp Family Singers (#Trappmusic). A few years later they settled in Vermont, the Austria of the U.S. (I mean, I’m sure someone has called it that), opened a mountaintop farm, and began hosting skiers.
That grew into a hotel and then that grew into a giant lodge on 2,500 acres. The Trapp Family Lodge (et al) is still managed by Maria & Georg von Trapp’s youngest child (of 10) Johannes and his family.
To start, we visited the Bierhall Restaurant and Brewery because it was, like, well past noon and we hadn’t hit up a craft brewery yet. Things were looking grim.
I’ve been enjoying the von Trapp Helles in Boston for years, every chance I get. Which is not that often actually. I love the von Trapp beers because they’re all Bavarian style lagers that take me back to the beer gardens and beer tents of my beloved Munich. *sigh*
The beers here are wunderbar, and the food menu is also sweet Bavarian goodness. They raise all their meats on the nearby von Trapp family farm and the burger I had was one of the best ever.
The brewery itself is located here on the property, as is a complete 18-hole disc golf course because Vermont. Beer to try: Natür Helles
Trapp Family Lodge
Afterwards, we visited the Trapp Family Lodge just a mile up the road. This lodge is a full-scale Alpine resort in the Green Mountains of Vermont and it is PRECIOUS Y’ALL. You definitely feel like the hills are alive here.
I have confidence I’ll stay here during my next weekend in Vermont. I do plan to climb every mountain after all. They’ve got the main lodge plus private Alpine villas so say So long, farewell! to regular ol’ hotels.
Book your stay: Trapp Family Lodge
11. Ben & Jerry’s ice cream factory tour
And, finally, no weekend in Vermont would be the technicolor dream world that it is without a visit to the home of Ben & Jerry’s. Well, not their actual home buuuut I don’t think living in an ice cream factory would be the worst way to live.
In a little town called Waterbury, Vermont you’ll find the Ben & Jerry’s ice cream factory, complete with factory tours, free samples, enormous portions, free range cows, ice cream puns out the wazoo, and even a flavor graveyard. Oh, and plenty of tie-dye.
Factory tours are offered 7 days a week, every day of the year except Thanksgiving, Christmas, and New Years Day. They last 30 minutes but only about half that is cow jokes. But let’s mooove on.
You’ll get to see the ice cream factory in action, learn about Ben & Jerry’s social commitments and the history of the brand, but also neat little tidbits like how Ben lacks a sense of smell and pretty much can’t taste anything. A trait seemingly better fit for a trash collector and less for an ice cream creator, but whatever.
After your tour you can hit up the Scoop Shop for full-size versions of your favorite flavor, fresh from the factory, you can visit the logo cows, many of the interesting *installations* around the property, and even the Flavor Graveyard, where Schweddy Balls go to die.
Have a 3-day weekend in Vermont?
Maybe you have a 3-day weekend in Vermont? (First of all, lucky!) There is plenty more to do there that I didn’t get to. Plenty more mountains to climb, beers to drink, and maple-y things to get your hair stuck in. Check out these other things to do in Vermont for your upcoming trip:
Morse Farm Maple Sugarworks, Montpelier
At Morse Farm Maple Sugarworks you can take free tours of the sugar house (with free maple syrup tastings), walk the nature trails, visit the country store, and take in the whole Morse Farm experience. If you’re operating on a Ross Geller-level of maple addiction, this is your place.
Vermont Teddy Bear Factory, Shelburne
The Vermont Teddy Bear Factory is one of the largest producers of Teddy bears, handcrafting about 500,000 each year. You can visit the factory, just outside Burlington, and even the Bear Hospital and it just doesn’t get any Vermont-cuter than that.
Lake Champlain Chocolates, Burlington
Look, I like factories, ok!? But this is a CHOCOLATE FACTORY. Hello? Scrumdillyumptious dreams come true! Check out Lake Champlain Chocolates while you’re in Vermont.
But what’s better than chocolate, ice cream, and maple? Cheese. Though the Cabot Creamery stopped offering factory tours in 2018 (it wasn’t me, I swear!), you can still visit and learn about cheese production and, more importantly, indulge in all the free samples.
Cold Hollow Cider Mill, Waterbury
Look, I think it’s obvious by this point that Vermonters like to consumer delicious things. But also, be super autumn-y too. Come to Cold Hollow Cider Mill for the sexy leaf colors, stay for your fair share of the 800 dozen cider donuts they bake PER DAY.
Quechee Hot Air Balloon Festival, Quechee
Spending a weekend in Vermont… in June? Check out the Quechee Hot Air Balloon Festival because, after Willy Wonka, the Wizard of Oz is a good one too.
Additionally, Vermont is huge on skiing. I, however, have never donned a pair of skis in my life. Snow nor water. Therefore, I cannot help you with this. But know that it’s there.
More info for your weekend in Vermont
What’s your favorite fall destination?
Let me know below!
But first, PIN ME ⇣⇣⇣