Flashback: it was March 13, 2020, and we were on our way to experience another beautiful Vermont winter ski trip, road-tripping in a Toyota Sienna despite the world closing down bit by bit. A mere hour from the U.S. border, all non-essential travel came to a halt. We pulled over, talked about the potential consequences of continuing, and ultimately turned around to come home. That Sienna sat in our driveway, packed with hope (and all of our ski gear), for another seven days before we reluctantly accepted that this virus thing wasn’t going away.
It was a full circle moment to finally make it back to Vermont, in a Sienna, this past March Break. And I’m so excited to share our itinerary — including a map below to help you plot your own adventure — so you can plan a Vermont road trip of your own next winter. To be clear: it doesn’t matter if you ski or snowboard; this Vermont winter itinerary has something for everyone.
So, buckle up and come along for the ride to see why you’ve got to add Vermont to your must-visit list.
Planning your Vermont winter itinerary
We’ve done this same Vermont winter ski pilgrimage for many March Breaks. At around six to seven hours one way from home, with various routes that include smooth highways, winding backroads, bridges with postcard views and even a potential ferry crossing in the mix, it makes for a stellar family road trip. But, as our kids get bigger, so does their ski equipment. What once would’ve fit into my CUV would now require a roof rack to transport.
Thankfully, the 2023 Toyota Sienna Hybrid 25th Anniversary Special Edition made its way into our lives and meant that we could get my kids, my parents and me plus our luggage and ski stuff into the trunk and in between the middle row with plenty of room for me to see out my rearview mirror. We’re talking six days’ worth of stuff for five people plus three sets of skis, boots, poles, goggles, base layers, outwear and more. (So. Much. More.)
OK, let’s talk itinerary planning. If you’re coming from the Greater Toronto Area, you can make your way to Vermont via New York or Quebec. My advice is to travel via Quebec if you’re starting your road trip in Northern Vermont, like we did at Smugglers’ Notch Resort. Then, come home via the New York ferry crossing between Grand Isle, VT, and Plattsburgh, NY, if you end your Vermont winter road trip in South Burlington, which makes the most sense if you follow our route in the map I created below.
The itinerary I’ve outlined here means you get a little bit of everything that’s quintessentially Vermont — mountainside experiences, Ben & Jerry’s, maple syrup and more — plus some U.S.-only bonuses for Canadians who dream of having daily access to the likes of Target and Trader Joe’s. It can be layered onto a longer road trip that encompasses more of the state (like the gorgeous and historic Warren, VT, for example) or customized for craft beer lovers, since Vermont is the craft beer capital of the United States.
Vermont winter road trip map
To help you plan your ideal route, I created a Google Map with all of the Vermont winter itinerary stops pinned:
We love a road trip with mountain views — like our British Columbia road trip last summer where we drove from Vancouver to Whistler and then uncovered sooooo many things to do on Vancouver Island — and Vermont is chock-full of them! There’s nothing like having a 4,000-foot mountain rise up on the horizon line as your elevation changes. This is the Appalachian Mountain system, after all, so those mountain views are guaranteed.
Yes, this is also a road trip built for those who love driving. And I’d be remiss here not to mention that the Sienna’s handling is perfectly suited for this kind of road trip since it can handle everything from long stretches to the tightest turns.
Vermont winter itinerary highlights
You can cover a lot of ground in just six days, especially if you don’t spend most of them skiing like we did. (But, really, what else are you supposed to do when 3.5 feet of snow falls in the first four days of your stay?!) One of the things I love about Vermont is how easy day trips are, even if you decide to ski for the morning and spend the afternoon going out and about.
That’s part of what makes Smugglers’ Notch Resort such an awesome home base; it’s in great proximity to everything on the map above, even if you decide to make Burlington a day trip instead of your route home. Plus, with condos that can accommodate up to 10 people, featuring full kitchens and free on-demand shuttles to take you anywhere at the resort — like the indoor swimming pools, two-floor kids’ play zone, Nordic centre, tubing runs and the main village with its restaurants, country store and Ben & Jerry’s outpost — you can bring grandparents along for some Vermont winter fun or share it with another family.
Alrighty, it’s time to walk you through this Vermont winter itinerary! We’re going to kick off this road trip in Northern Vermont between Jeffersonville and Johnson, then work our way to Burlington via Stowe and Waterbury…and since some people prefer a video format, I put together a highlight reel of the itinerary (but don’t worry, Type As — your detailed overview is alive and well below; just keep scrolling).
Things to do in Jeffersonville (Vermont)
Starting in Jeffersonville, where Smuggs is located, there’s enough to keep you busy here for a whole week if you maximize what’s at the resort:
- Three mountains on which you can ski and snowboard, with progressive difficulty (fun fact: Smuggs is home to the only triple black diamond run in North America) and loads of backcountry options. In case you’re looking, some of the best places to ski in the trees is actually on Morse Mountain, just to the right when you get off at midstation, and plenty more over in the Highlands area
- Night School — learn a new snow skill! We tried snowboarding and the 1.5-hour lesson and rentals combined was only US$75 per person
- Tubing — there are two tubing locations at Smuggs; one for afternoon tubing and one for evening tubing. It’s loads of fun and we suggest wearing your goggles overtop of your winter hat if you want to see while tubing
- Swimming — Smuggs is home to a number of indoor heated pools and hot tubs
- You can also just wander around and enjoy village life — or stop to people watch while enjoying a hot cocoa sitting at one of the working fire pits
- FunZone 2.0 — do NOT forget your kids’ running shoes like we did or they won’t be able to use the Ozone section of the FunZone space, which is where the climbing wall and laser tag live
- CatTrax Tour — for US$69 per person, this is a really neat experience (especially for people like my parents who would otherwise never have the opportunity to stare down a ski run from the summit). Up to 12 people can ride up the mountain in a modified groomer, which has a heated cab added to its back end
- You won’t go hungry at Smuggs; there’s a Country Store, Ben & Jerry’s and full-service restaurants in the main village at the base of Morse Mountain plus over in between the Sterling and Madonna Mountain lifts. The Hearth & Candle deserves a special shout-out for being one of the only fine-dining restaurants I know of where you can saunter in wearing just about anything and no one will look at you sideways
- Fireworks — every Thursday night all winter long
Branching out from your home-away-from-home at Smuggs, here are some other spots to hit nearby:
- Vermont Maple Outlet — we stock up here on the darkest maple syrup (but they sell all four kinds) because the prices are really good and you can get HUGE jugs of the sweet stuff
- Wyckoff Family Maple — new since our last visit, this gourmet sugar shack looks like a million bucks and if Mr. Wyckoff didn’t build it himself by hand, it probably would have cost that much to erect. There isn’t a single nail to be found in the joint — the entire structure uses only wood and old-fashioned engineering to stay standing. Be sure to pop in and do a syrup tasting with any of the nine flavour-infused options (we took home the bourbon and cardamom syrups)
- The Family Table — a great new restaurant in Jeffersonville (have the calamari)
- Brewster River Pub & Brewery — accessible by the Smuggs shuttle, even though it’s not technically on Smugglers’ Notch Resort property, this lively pub is one of my family’s favourites
Note that in the summer months, there’s even more to do in Jeffersonville, but since this is all about a Vermont winter visit, you’ll have to wait for a summer itinerary or go rogue and explore on your own.
Things to do in Johnson (Vermont)
Nearby Johnson is absolutely lovely to visit in warmer weather (you can actually get there by bike on a rail trail from Smuggs), but in winter, it’s our favourite place to stock up on groceries and beer, wine and alcohol when we stay at Smuggs.
Although the shopping in Cambridge is closer ,Johnson’s Sterling Market — and its connected liquor/beer store — has the best selection for groceries, including homemade breads, farm-fresh milk and some organic products. And alllllll the Cabot Cheese!
The Farm Store serves our favourite fancy coffees and has the yummiest baked goods, so that’s also worth visiting during your Vermont winter vacation — especially if you’ll be nearby shopping at Johnson’s.
Things to do in Stowe (Vermont)
Stowe — known as the ski capital of the east and the birthplace of ski patrolling — is a quintessential example of an historic New England town, with the first of its buildings going up in 1811. Although the local household income isn’t one of wealth, Stowe is home to some of the priciest homes in the USA thanks to its proximity to Mount Mansfield, which is where alpine skiing first took shape in North America.
Just driving along highway VT-108 as you come through Stowe, you’ll see an immediate shift. The old and sometimes colourful homes become grander and more stately, and you’ll eventually come upon downtown Stowe, fully of shops and restaurants that could easily take half a day to explore should you opt to make this a day trip from Jeffersonville. Be sure to pop into Remarkable Things at Stowe Craft for an eclectic selection of giftables and collectibles while you’re here.
If you get hungry in Stowe, one of our favourite restaurants downtown is Doc Ponds. But if you’re up for some more driving, I’d encourage you to have a poke around the Trapp Family Lodge grounds. If “Trapp” sounds familiar, von Trapp surely will. Yes, yes — those von Trapps, from the Sound of Music. This place is actually still owned and managed by two of Maria and the Captain’s grandchildren and it’s an absolute must-visit. We go every time we’re in Vermont because it’s such a special place. Here, you can grab a coffee (and pastry and even the von Trapp’s own eggs) at the Trapp Kaffeehaus or enjoy a meal at the von Trapp Brewery & Bierhall (the ale and cheddar soup is too good for words).
Before you leave Stowe, though, make sure you take a drive through The Lodge at Spruce Peak — the only Stowe Mountain Resort mountainside lodging available for guest rentals. It’s technically across the street but has direct mountain access via an exclusive gondola from The Lodge. We were supposed to stay here in 2020, and I vow to get there again to tell you more about this gem.
Things to do in Waterbury (Vermont)
With the first permanent white settler arriving in 1783 and The Central Vermont Railroad arriving in Waterbury in 1849, this town became a commercial hub. All these years later, Waterbury is home to Ben & Jerry’s — Vermont’s most popular tourist attraction. Even in winter, it needs to be on your list!
Ben & Jerry’s HQ offers tours, and you should book your tickets in advance if you have your heart set on a certain date and time. If you don’t care about the full history, and trying the daily “secret” ice cream available at the end of every tour, you can certainly still spend some time here taking in the experience. They’ve done a great job making it fun and interactive for customers just passing through who aren’t doing the tour. Plus, it has the most ice cream flavours you’ll find at any Ben & Jerry’s location — and we’ve never seen them run out of a flavour like they can at the various outposts. (My all-time fave? Cherry Garcia. Try it!)
While you’re in the neighbourhood, I also suggest visiting these three places, which are all within an easy walk of each other once you park:
- Cabot Creamery — all things Cabot cheese and butter (so good)
- Smugglers’ Notch Distillery — you’ll see “smugglers’ notch” used repeatedly in Vermont, which capitalizes on its place in the prohibition history books. This distiller crafts a number of spirits and liqueurs, and a tasting is definitely in order if you stop by
- Lake Champlain Chocolates — the Waterbury location has a full selection of the brand’s yummy chocolates, a hot chocolate and espresso café bar, homemade ice cream and even factory seconds if you’re a deal-hunter
Things to do in Burlington (Vermont)
On the eastern shore of Lake Champlain, next to New York and just southeast of the Canadian border — in what is surprisingly not the state capital — Burlington is Vermont’s hot spot with the biggest population and the most stuff. From gyms and big box stores to restaurants and lots of hotels, Burlington is also home to the main airport. If you’re flying in for your Vermont winter vacay, you’re probably going to fly into Burlington. (Just make sure you’ve got a car rental or private driver waiting for you, because it’s shocking that those are basically the only options to get out to the state’s various ski resorts.)
Is there a Burlington Coat Factory here? Friends, I still don’t know. It’s a question I ask myself every time I visit but don’t really care enough to Google. (Three cheers for random thoughts.)
What I do know is that there’s both a Trader Joe’s and a Target in Burlington. The Target isn’t the best one you’ll find in the eastern US, but when in Burlington…worth it. But the real star of the show here is Trader Joe’s; we love this place! There are so many good reasons Trader Joe’s is a cult favourite among Canadians and unless you want to pay crazy markups to get the goods via Amazon, it’s best to go straight to the source. Stock up on our personal favourites like the brand’s shampoo bar, shave cream, dark chocolate peanut butter cups, Everything But the Bagel seasoning, Bourbon vanilla extract, cacao-dusted almonds and the chili-lime rolled tortilla chips, among others.
If you end up heading back to the Toronto area via Burlington (by taking the long way like we did so we could hit Stowe and Waterbury en route), you’ll have a long day of driving ahead of you. And if you’re sporting something like the all-new 25th Anniversary Special Edition Toyota Sienna Hybrid, you’ll be doing in very comfortably.
Here are just a few final reasons we loved driving the Sienna to Vermont this past winter:
- The turn-by-turn directions appear both on the display AND on the dash, keeping my eyes on the road and my back-seat drivers pacified
- The 12-speaker JBL audio system
- Wireless smartphone charging between the two front seats
- Enough USB and USB-C ports to keep the whole family connected while in transit
- An ability to customize everyone’s ride, especially when it comes to heating and cooling. The Toyota Sienna Hybrid makes this especially easy with front and rear climate controls right at the driver’s fingertips
- Dynamic Radar Cruise Control — tied with the kick-open trunk and side doors, this is my absolute favourite feature! Once you set your cruising speed, the Sienna’s built-in dynamic radar adjusts to the vehicle’s speed ahead of you to ensure you never get too close too fast
- It’s got CarPlay! As soon as I enabled my iPhone, it built a seamless bridge to the Sienna’s display
But I need to extrapolate on the CarPlay front here and give you a pro tip when it comes to the Sienna’s built-in navigation assistance; if you have data available to you in the USA, be sure to use CarPlay to access Apple Maps, Google Maps or the Waze app on your iPhone. While the Sienna’s directions were spot on 95 per cent of the time, we had two occasions where Waze was the better way to go since it knew about a seasonal road closure in Stowe and the ferry crossing between Vermont and New York, and the nav system didn’t. It doesn’t mean you won’t get to your destination — it just means that you could be more efficient using CarPlay.
Toyota Sienna 25th Anniversary Special Edition — hybrid fuel efficiency
Yep, the Toyota Sienna continues to be so freaking impressive when it comes to fuel efficiency that I’m closing out this post by giving it it’s own section.
In all, we travelled 1,624 kilometres and — thanks to the Sienna’s hybrid system, which charges the battery while you drive (no need for plugs!) — we only stopped for gas twice and spent $120 plus change (Canadian!). I mean, that’s seriously impressive. All said and done, bells and whistles aside, THAT is what makes the Sienna a consistent road-tripping dream.
Just can’t get enough of Vermont? Here are some additional posts of mine you may want to read next:
- 4 places to go spring skiing in Northern Vermont
- Smugglers’ Notch skiing & lesson info
- 8 things to do at Smugglers’ Notch Resort this winter
Have more Vermont winter itinerary suggestions? Feel free to leave them in the comments. Happy road tripping!
DISCLAIMER: Toyota Canada compensated me for this post. All itinerary suggestions and vehicle observations and opinions are my own.
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