Slopes, Laughs and Après: Learning to Ski on a Vermont Momcation

I’m back from my first trip for 2025 and I decided to something very unusual for me. I accepted an invitation to join a ski themed girls’ trip to Vermont. You’re right, I’m not a skier. I figured there are so many fun things to do in Vermont during the winter that if I hated skiing, I’d still  be entertained. I was right, I’ll have you know! Vermont is truly magical when it’s covered in snow and the locals know how to have a great time even in the midst of a snowfall. I also came to  learn that I might actually enjoy skiing! Read on and I’ll share our Vermont winter itinerary and a list of Vermont winter experiences you shouldn’t miss out on your next winter road trip!

 

Disclosure : This post is in partnership with Ski Vermont but, opinions are TOTALLY ours, as always. 

 

Girls’ Trip to Vermont This Winter :

Where to Stay, Eat & Play

Things to do in Vermont on a Momcation

 

We drove from Toronto to Vermont for our 7 day trip and stayed in a couple different spots, taking in  the Vermont winter activities and enjoying the après ski entertainment.  I joined Andrea from Mommy Gearest and Lauren from Justin Plus Lauren for this Vermont girls’ getaway and our ride for the week was the 2025 Honda Pilot Trailsport (thank you Honda Canada for the loaner). I was a passenger princess as always, enjoying the heated seats and controlling the temperature on our snowy drives even when I was seated in the back. 

 

Table of Contents

Where to Stay in Vermont

Things to do in Vermont on a Girls’ Trip

7 Day Itinerary

 

Where to Stay on Girls’ Weekend in Vermont

The main goal for this trip was for me to experiment with skiing. Andrea is an avid skier and she got me on a horse a few months ago so she was determined to get me on skis this time around. The below Vermont hotels are all great options if you’re looking to mix in some ski lessons and relaxation whilst also exploring the nearby areas. 

 

Trapp Family Lodge

Trapp Lodge Sunrise

If you’re a Sound of Music fan like I am, you will most definitely want to add a stay at this Vermont ski resort to your Vermont itinerary. Yes folks, Maria was a real person and she ended up in Vermont once she and the Captain fled Austria with the kids. What you might not know is that Maria and the Captain had three kids together and you can find their son and his family running the Trapp Family Lodge today. I’ve had the great fortune of meeting two of Maria’s grandchildren and on this trip I learned more about Maria’s life in Vermont and how the family continues to celebrate their Austrian culture. 

 

The Trapp Family Lodge is located in Stowe, Vermont (one of Chris’ favourite areas in Vermont due to its proximity to one of his all time favourite breweries) and sits on a 2,600-acre property. The resort operates all year-around and offer 96 rooms and suites in their main lodge as well as luxurious villas and guest house chalets. On this Vermont girls’ trip I stayed in the main lodge and loved the many welcoming spaces. They have sunlit reading nooks, numerous fireplaces to get cozy around and corners to play board games at (they have many games for your enjoyment). During our winter visit the entire space was adorned with fresh flowers that really brightened up the vibe and they had a Christmas tree in every room (they were taking those down the day we checked out!). 

 

My room was spacious, had a cozy cabin vibe and had everything I needed. The bed was comfortable, yet I woke up in time to catch sunrise from my snow covered balcony and it was magical. 

When you stay at the Trapp Family Lodge, you have access to their daily tours (public have to pay for it but it’s included in the resort fee for hotel guests) and I highly recommend taking a few of them. During our visit we went on a walk to meet the Highland Cattle who live on the farm and we took a history tour that told us the REAL family history. The tour is how I came to appreciate the little details throughout the property- like the carpets that pay homage to the Captain’s defiance of the Nazi regime. I also encourage you to catch a viewing of the “Real Maria” which is a 20 minute documentary that lodge guests have access to. 

I knew guests have trail access and could rent snowshoes or go cross country skiing here but I absolutely missed visiting their indoor climbing wall and their awesome looking pool during our visit. I definitely want to return with Chris and the kids to enjoy a longer stay here and immerse ourselves in all the winter activities onsite. They also have a spa onsite and a variety of classes on offer (from yoga to knitting). 

As I mentioned earlier, we enjoyed a lovely chat with Kristina, Maria’s granddaughter and the family’s passion for recreating a mini Austrian experience in Vermont is strong! She and her brother (and their father) are very hands-on and you can tell that every staff member is like family here. We enjoyed a fantastic breakfast in their dining room and while we didn’t have dinner here, we did enjoy some live piano music on our first evening in Vermont. 

Even if you’re not staying at the Trapp Family Lodge, you should plan to dine at the Von Trapp Brewing Bierhall. The Bierhall is a gathering place for friends to enjoy “a little of Austria, a lot of Vermont,” serving fresh lagers and a selection of freshly prepared Austrian lunch and dinner options. Many of the menu items are prepared on the wood-fired Parrilla grill and yes, you need to get the crazy large grill platter that will easily feed 4 very hungry people! 

As you can see, our stay at this Vermont ski lodge was truly magical and I highly recommend a stay here (no matter the season to be honest), especially if you appreciate history. You guys, you can go pay your respects to Maria who is buried by the main lodge!!! 

I will also quickly mention that you’re in Stowe and there’s many thing to do in the nearby area! 

 

Mountain Top Inn

Mountain Top Inn

For those looking to mix relation and XC skiing, this is where you want to be! Centrally located in Chittenden, Vermont this resort is perched on the top of a mountain and offers a variety of on-site activities – which might explain their motto “Come for the View, Stay for the Experience”.  

If you’re curious about the history here, you should know that this property used to be known at the Mountain Top Inn and began as a converted barn from the Long family’s turnip farm which was founded in the 1870s. Mr. William Barstow (who was an associate of Thomas Edison) purchased the farm as a gift for his wife who was always entertaining a variety of her NYC guests. As things happen, the family kept expanding the lodgings as more and more guests joined them–eventually evolving into a full service Inn & Tavern. The Wolfes purchased the property in 1945 and President Eisenhower stayed here during one of his fishing expeditions. The ‘Ike’s View’ room in the Main Lodge is aptly nicknamed for him. It was the Wolfes who developed a cross country ski center and trail system. Today, the trails are one of the oldest in the country and everyone can enjoy the 60KMs of trails

 

Let me start off by saying that it was here that I did my first cross country ski lesson and the instructor was absolutely fantastic! Even if you’re not staying here, taking a lesson or two with Mary Anne will help you up your XC skiing game! You can rent everything you need at the resort’s Activities Centre, making it easy whether you want to snowshoe or cross country ski. Mary Anne and the team were patient and helped us all find our right sizes for ski boots and poles. Once we were out on the trails (your trail pass is included when you stay at Mountain Top Resort), Mary Anne got me comfortable and put my fears to ease. I had just received the all clear from my surgeon two days before so this was my very first activity after the hysterectomy. Given that I had not done any sort of workouts for over 9 months, I think I did pretty awesome! 

We also snowshoed for a minute before we got distracted!

Even if you’re not an overnight guest at Mountain Top Resort in Vermont, you can enjoy their USD 200 sleigh ride and 3 course dinner package. Yes! My girls and I enjoyed a picture-perfect, movie-scene-worthy snowy carriage ride! And yes, the horses were Belgian horses who are able to perform draft work in a healthy manner. 

 

During our two nights at at the Mountain Top Resort I enjoyed the comforts of my suite in the main Lodge. While the king bed was a lovely luxury, it was the stand alone soaker tub that I enjoyed the most! The walk-in shower also had multiple shower heads which also gave me ideas for our next home. As you can see from the pictures, I had a kitchenette, microwave, 2 TVs, fridge and glassware.  

Each night the girls would come over for a nightcap at mine because I was the only one in a suite and I had a two-sided fireplace to keep us all toasty. 

I roamed around the Lodge and  saw that they have multiple room layouts so there’s something for everyone! I didn’t see the cabins or guest houses but did gather that families would enjoy the spacious guest houses. Just know that you need winter tires to get to the guest houses and cabins because there was a lot of snow during our visit and not all roads were paved. 

When you stay at Mountain Top Inn there are even more activities you could enjoy. After my ski lesson I went straight for a massage at the on-site Blush Vermont Spa and that was such a brilliant idea because I had ZERO pain after my 1.5 hour ski session! I’ve never seen showers in the massage room before this trip but now I have!

I didn’t use it though because I wanted to enjoy their outdoor hot tub! I forgot my hat but it was kinda cool to see  my hair freeze (and realize what I’d look like with a full head of white hair). The hot tub and sauna are available for guests to use but know that you do have to go outdoors to access the spa area-and the resort does not have bathrobes in the room. The spa does have bathrobes though!! I received one after my massage and it kept me warm enough to go from the hot tub back to the Lodge and into my room. 

person sledding at Vermont Hotel

Not only did I take my first  cross country ski lesson here, but Andrea encouraged me to sled for the first time. The resort has a small hill with sleds parked for guests to use so it was easy to be carefree and yell “yippee” as I raced towards the unknown. 

We enjoyed quite a few meals here and PLEASE try their maple butter during your breakfasts and definitely get their cornbread at dinner because it was REAL good. I’m craving some as I sit here in Toronto reminiscing about this girls’ trip to Vermont. I was also impressed by the cocktails at the Mountain Top Tavern because they had a full bar and the bartender was busy shaking up cocktail after cocktail during our dinner seating. It does get busy here so I definitely recommend making reservations if you know you want to stay indoors and not venture off resort for your meals. That said, you’re not too far from Killington so there are options within a 20 minute drive if you do want to explore. 

 

Killington Grand Hotel

If you’re looking for that true downhill skiing experience, this is the place to be. This full service mountain-side ski hotel in Vermont enables guests to easily walk to the slopes from their hotel (there’s a bridge connecting the hotel and the slopes). As soon as we drove in we were informed that the valet parking was complimentary and thus, we handed the keys to the Honda Pilot and didn’t touch them again until our departure because the hotel and resort has complimentary shuttles that took us to the various places we wanted to explore. 

My hotel room at the Grand was fairly basic and as you know, I’m not a fan of the two bed configuration when I travel solo, but I must admit that it was nice to have that extra bed to crash on while wearing my “outside clothes” after a sweaty ski session. 

I also requested for a mini fridge so I could store the cold beers I had purchased for Chris at the various places I stopped in at. Chris is very particular about his Vermont beers and when they’ve been purchased cold, you need to keep them cold. And no, the snow filled balcony attached to my room would not have worked because it would have frozen the precious brews! I will also mention that you are on a resort and while you can purchase items on-site they come at a premium price (so stock up on room snacks and bevvies ahead of arrival if you’re on a budget).

When it comes to amenities at the Killington Grand Hotel, the highlight for me is their year-around outdoor pool and hot tub. After a day of skiing, soaking your bones in that hot tub with views of the mountain as your backdrop-is magic! The hot tubs definitely get busy on weekend evenings (so busy that I couldn’t fathom squishing myself in when I attempted to on a Saturday) so my recommendation is to sneak in a late afternoon session. You can swim from indoors so that bathrobe (yes they have bathrobes in your rooms!!) can stay dry and warm if you wish! 

In addition to a gym there was a games room-so you can entertain yourself any way you want! There’s a tuck shop and cafe selling various drinks, snacks and even souvenirs- get the peanut butter chocolate balls when you’re here!!

The Preston’s Restaurant and Bar is an easy spot to enjoy breakfast and dinner at. We had a meal here after a day of skiing and I really enjoyed the corned beef at breakfast. 

They also have a laundry room and a spa but let’s talk about the skiing shall we? You can check your skis and poles at the ski check area in the hotel so you only have to take your boots to the room. They also a have a bridge that gets you from the hotel right to the slopes and the chair lifts. 

We were on a Vermont momcation but I couldn’t help but notice the kids enjoying themselves here at the Grand Hotel – there’s plenty on offer for all ages (see that ping pong table?). Oh and I almost forgot to mention, hotel guests can enjoy the free shuttle services to get you around Killington! 

During our two night stay at this Vermont ski resort we truly embraced the Après vibes on offer throughout the resort and I’ll share more about the things we did at Killington in the section below! 

 

 

Things to do in Vermont on a Winter Momcation

girls trip shopping in Vermont

Listen, let me tell you, there’s no shortage of things to do in Vermont on a winter girls’ trip. I’ve been to Vermont a couple times and wasn’t really sure we’d get up to much in the winter and boy was I wrong! We found so many Vermont winter activities that I didn’t get in as much relaxation time as anticipated. All that work I was planning to catch up on whilst watching the snow fall outside my window, never happened because curiosity got the better of me and the girls and I simply HAD to explore! 

 

Explore Stowe

If you haven’t heard about this charming New England town, you’re missing out on some fun activities! I’ve spent  many a summer day here (I mean it is home to one of the world’s best ice cream headquarters after all!!) but I was delighted to discover that Stowe is an active Vermont town even in the middle of winter. For those staying at the Trapp Family Lodge, these explorations are very close by.

If you’re a craft beer fan then you most definitely have heard of the family owned Alchemist. Back in the day, folks like Chris would wake up at the crack of dawn to get their fingers on Heady Topper, but it’s far easier now because you can visit the beer cafe and sip on a variety of offerings. I absolutely loved the artwork here and I know Chris will want to linger here for a couple hours on our next visit. On this girls’ trip, Lauren and I enjoyed a quick cold brew because we knew our next stop was calling our name! 

It’s shopping time y’all! Downtown Stowe certainly delivers that quintessential cutesy Hallmark town vibe. I recommend stopping in at Aladdin for some Middle Eastern fare before you start your strolls. Having grown up in the Middle East, it always makes me happy to see a taste of home during my travels. I didn’t expect to stumble upon a vegetarian spot serving hearty hummus bowls and roasted cauliflower pita sandwiches, so this was a real treat! 

If you like checking out the American beverage alcohol shops like I do, let me mention that there’s a cute spot next to Aladdin that’s worth poking your head into. 

Not to worry, downtown Stowe’s main street is very close by if you would rather check out cool stationery, cute souvenirs and charming bookstores. Just stroll along Main Street and you’ll bump into spots like the Stowe Mercantile, Northwood Gallery and Shaw’s General Store. We didn’t get to the Ski and Snowboard museum, but if you’re on a mission to immerse yourself in all things winter, this might be a great spot to spend an hour at. 

I’ve done the Ben & Jerry’s ice cream tour on a couple occasions and on this visit, we only popped in for a quick treat because it was getting dark and we wanted to return to the lodge before nightfall. A word of caution, winter driving can be tough and even though we had the snow mode on the 2025 Honda Pilot to help the car maintain stability and grip on slippery roads, it can be still be quite dicey, especially on roads you’re not familiar with. So we recommend getting back to your lodging before it gets too dark if you’re a bit leery about winter driving. 

 

Learn to Ski

Yashy and Mommy Gearest skiing in Vermont

I couldn’t have picked a better place to learn to properly ski. Vermont is filled with skilled skiers who are eager to teach you and there’s such a welcoming vibe on the beginner slopes and trails. As I mentioned earlier, I took a cross country ski lesson at Mountain Top Resort but I also took a 3 hour downhill ski lesson at Killington Resort.

At Killington they have everything to help you have a perfect day on the slopes. I recommend going a day early to get your ski boots fitted if you plan to rent them. It took me two tries to really figure out the right boot size. Also, please learn from me and bring proper ski socks with you -your unmarked shins will thank you. The staff at the rental spot were fabulous and got me comfortable with the gear so I wasn’t THAT clumsy by the time I shimmied myself up to the beginner lesson meeting point. 

We had a couple instructors teach us how to maneuver on skis and I impressed even myself because I voluntarily went up the magic carpet and down the slightly bigger (but still beginner) hill by the end of the 2nd hour. If you’re taking lessons, know that they have beginner lessons just for adults (so you won’t be grouped in with young kids) and your lessons include equipment rentals and a limited learning area lift ticket, providing access to Snowshed and Ramshead lifts. Because we were staying three nights at Killington Grand we received our ONE PASS, RFID card at check-in but if you plan on a day visit, you will need to purchase the card for about 6USD. This card is what you’ll need to access your lessons and any other activities you book. 

Yashy and Andrea in Vermont

I was confident enough after my 3 hour lesson that I decided to take Andrea’s suggestion of joining her (she’s an avid Skier) on the ski lift to hit a REAL green trail the following day. Well, let me tell you, getting off a ski lift wearing skis is no easy task. I wholeheartedly face planted and unfortunately no one had a camera to capture that. No bruised egos- everyone propped me back up and got my boots back into the skis so we could make our way down the slopes. I fell again and Andrea was patient as she helped me fine tune my turns and taught me how to slow down as I went down the hill. You guys, by the time I came to the beginner hill which was our exit route, that beginner hill I found daunting on the morning run was a piece of cake come late afternoon. I won’t be saying no to an afternoon at a ski hill the next time the opportunity comes knocking. If I can get my 44 year old, 94 Kg body on skis for the first time and have fun, trust me – you can do it too!!! This brown girl knows to ski after a few days on the Vermont slopes! Yeeehaw! Surround yourself with friends who encourage you to try new things!!!! 

 

Spend the Day at Killington Resort

Ski vermont with moms

They say Vermont is winter in its natural state and I can certainly attest to that. Just look at these views!!! I know I’ve mentioned this resort a fair bit already but I still have more to tell you! So listen up, okay? As I’ve mentioned earlier, the Grand hotel is the accommodation of choice if you’re looking to stay on the resort and you can take ski lessons here at the resort too. But did you know that there’s about 18 eateries and various Après ski activities too? Known as the “Beast of the East”, this Vermont ski resort truly does have it all and, guests of the Grand Hotel can access all of the amenities. 

I enjoyed lunch at the Long Trail Pub which was right by the beginner hill and it was a tasty and hearty meal. The perfect option after my ski lessons on that first day. They have live music on weekends too if you’re looking for that vibe. 

I also returned here for evening drinks and this was my real introduction to the Après ski vibes – everyone was tired but happy as they sipped their drinks and enjoyed some friendly banter with fellow ski friends. This spot does close at 6 p.m. so keep that in mind! 

woman tubing at park in Vermont

If you’re a kid at heart you’ll certainly want to take a spin at their tubing park. Tickets do have to be purchased for this activity(goes on your OnePASS) and I enjoyed the fact that I didn’t have to walk up the hill after tubing down because they have a magic carpets that bring you and your tube up the hill! 

Whatever you do, don’t ignore the Peak dining lodge. While there are quite a few eateries that are only available to skiers who can make their way up some of the harder trails, dining at 4,241 ft isn’t just for the professional skiers- luckily! You can take the K-1 Express Gondola up and here’s a tip – there’s a different line for those not on skis and it usually has a shorter wait! For non-skiers and snowboarders, they offer round-trip K-1 Express Gondola tickets (which must be purchased online), to get you to and from this one-of-a-kind dining experience. It’s only open until mid afternoon and trust me when I say, the journey there is quite magical. Pristine snow covered trees greet you when you get to the top and the dining room has some solid options. It was crazy busy when we were there but we didn’t have to wait more than 15 minutes for a table – everyone hovers around those who look like they’re nearly done and grab the vacated table at this fancy cafeteria! 

I didn’t do this but Mommy Gearest did, and she recommends downloading the Killington App, especially if you’re looking to keep track of your runs. I will also mention that the resort is quite large and you may want to make use of the free busses that loop around the resort. The Grand Hotel had a TV showing bus schedules with live updates but that wasn’t always available elsewhere around the resort. 

I’ve mentioned the winter activities on offer at this Vermont ski resort, but know that they have fun summer activities if you’re looking to visit off season! 

If you’re looking to dine off resort, I’ve shared about the Wobbly Barn below but I’d also like you to consider Yama Ramen. It’s a cozy, sit down but quick service spot serving some pretty darn good Ramen and even have a vegan broth for those that prefer that! 

If you want to shop for some REALLY REALLY nice or funny cute stuff, head to the Greenbrier Inn and Gift Shop which is an easy five minute drive from the resort. We could have spent 2 hours just roaming around the shop because they had the craziest collection of everything! I was so tempted to buy Christmas gifts in January but I did not – be impressed! 

 

Enjoy the Vermont Nightlife 

ladies having drinks in Vermont

When you think of a winter trip in Vermont you may not really think about venturing off for some late night entertainment but if you’re in the Killington area, it’s definitely a great option. Because we were staying at the Grand hotel, we had access to a free shuttle that would take us around Killington and we also discovered that places like Pickle Barrel (no affiliation with the Canadian chain) had their own free shuttles that would drop and pick you up. What a wonderful way to drink responsibly and get home safely! Just remember to tip your driver.

 

With access to these free transportation options, it’s easy to enjoy the nightlife and live music. The three of us had some fun times on the dance floor at the Wobbly Barn (which is part of the Killington Resort). If time permit you can have dinner at the Wobbly Barn’s Steakhouse which will give you free entry to the “nightclub”. The Wobbly Barn is very popular and they don’t accept reservations so we weren’t surprised when we had a 30 minute wait for the table. The locals did warn us but they also told us we HAD to dine here. We like to listen to locals! 

I quickly came to realize that the word “nightclub” is used a bit freely in Vermont. Don’t think of the multi-floor, lights thumping in your face scenarios you might be used to in Toronto. Think more of a barn vibe where you’ll want to have a beer in hand whilst listening to visiting bands like Changing Lanes from New Jersey. All the night spots we swung by had cover charges so keep that in mind. I found it fascinating that there was quite the mix of ages here on the Saturday night-from local students to moms like us and even some folks who were older. Everyone was having a good time!

Turning the Tide band was performing the night we swung by the Pickle Barrel one evening and they were totally rocking the place that Friday night. This spot also serves pizza and I was told them pump out over 100 pies on a good night! We’d dined at the ramen spot nearby so unfortunately I did not order anything but I can see it being absolutely fabulous after a few rounds of drinks! 

If you’re looking for more of a sports bar vibe, then Jax Killington is where you want to head to. They also had live music when we swung by but it was the gaming area that caught my attention. 

As you can see, there’s multiple ways to enjoy the nightlife in the Killington area but trust me when I say other parts of Vermont also have a similar vibe if you’re looking to dance the night away. My nights out took me back to my college days in Maine because it was the exact same vibe (something very different to the Toronto nightlife scene!). 

 

Visit Maple Farms

Listen I know Ontario and Quebec have some liquid gold but can I encourage you to visit a Vermont Maple Farm? Not only is it picturesque but if you visit a spot like Baird Farm, you might just luck out with a quick tour of the property and a free sampling! This working family farm in Chittenden has been in the Baird family for four generations. 

We reached out to them via Instagram to see if they might be open and lucked out by meeting one of the family  members who was a fun character. Bonnie and Bob Baird own and operate the farm today while their daughter Jenna and her partner Jacob run the maple syrup business. It was Jacob who took us around and even let us tap a tree!

Through our conversations we learned about the VERY DARK maple syrup which is very hard to find in general and not available at all in Ontario (at least not commercially). From what I understood, the syrup is darkest towards the end of the sugaring season and it reminded me of Sri Lankan treacle (which is made from the sap of the Kithul Palm). 

If you’re staying at the Trapp Family Lodge, they had some Maple Sugar Tours that required you to snowshoe around their property! Alternatively, not too far from Mountain Top and Killington is Sugar & Spice, a restaurant and maple shack which serves breakfast all day long. This rustic sugar house is a really good spot to warm up at if you’re looking to enjoy some maple syrup and pancakes or a hearty meal! The sugaring production wasn’t happening during our early morning visit but we were told that they had just made some fresh maple candy when we walked in! 

 

Explore the Many Cute Vermont Towns

driving in Vermont looking for things to do

As we rode around Vermont in our Diffused Sky Pearl 2025 Honda Pilot, we couldn’t help but squeal ” Oh that looks so cute!”  “Oh can we please stop here for a quick pic?” “This looks so preeeety!” “I think I have a Christmas card with this exact winter scene”. We drove through many cute towns and often stopped for a quick bite or to peruse the stores. Below  are some of our favourite stops. 

 

Rutland: Downtown Rutland, known as the city of murals, showcased its vibrant street art as we spotted several during our evening visit for dinner at Roots restaurant.  The Cheese Fondue with Apples was SO good as was the Lobster Risotto. Our vegan friend was also able to find a variety of options she could enjoy.

Our meal was fantastic and the service was top notch.

If time permits, pop into stores like Phoenix Books and Divine. Rutland is an easy 2o minute drive from both Killington and Mountain Top Inn. 

 

 

Weston : I’ll be honest here, this is a cute town but you’re heading here mainly to visit the Vermont Country store. The store which has been around since 1946, is family owned and operated. There’s many country stores peppered throughout Vermont but this one is epic in size, quality and offerings.

You’ll easily spend an hour here and not even notice the time go by. They have everything from snacks to clothing, making is a great spot to buy some gifts for yourself or loved ones. Typical of New England houses, the family has been expanding their space by adding on rooms over the years and you actually enter from the back of the house and you head into the more historic parts of the shop as you go further in! Oh and by the way, Weston is about a 45 minute drive from Killington and and hour from Mountain Top Inn.

 

Manchester : Of all the towns we explored, this one is quite possibly my most favourite and to be honest, it’s really a city and has loads of fun things to do when in Vermont. It is about an hour away from Killington Resort and Mountain Top Inn, which makes it a great full day trip or you can stop in on your drive home if you’re heading back to Toronto. 

Okay, so when you’re in Manchester, you might want to spend at least an hour at Hildene. This historic estate in Manchester, Vermont, is best known as the former summer home of Robert Todd Lincoln, the only surviving son of Abraham Lincoln. I encourage you to take a tour because the little details are fascinating and so forward thinking. Yes, you can see President Lincoln’s top hat here! No, you cannot try it on. The welcome center here is filled with lovely artwork and design forward items so it’s worth a quick peruse through as you purchase your tickets. IF time permits, you can wander around the grounds to visit the on-site farm and the Pullman car. During our cold winter visit, we much preferred to stay indoors! 

Downtown Manchester is home to cute gift shops like Aunt Bonnie’s and some fabulous eateries. We enjoyed a delicious lunch at Thai Basil and let me tell you, that bowl of Beef Massaman (I asked for it to be made spicy) really warmed the cockles of my heart.

Whatever you do, definitely plan to stroll around the family owned Northshire bookstore (which has plenty of items for sale beyond books) and enjoy a drink at the Colburne Cafe inside!

 

The 2025 Honda Pilot Trailsport certainly got us around Vermont! It had ample space for all of Andrea’s snow gear and all of our suitcases (and shopping). 

 

The Ultimate Vermont Winter Girls’ Getaway Itinerary

7 day Vermont Itinerary

I’m quite sure that your list of things to do in Vermont is getting insanely long at this point, but hey, we incorporated all of these Vermont activities into our 7 day Vermont itinerary, so you can do it too! Of course, if you prefer to relax a bit more than we did, then cut out an activity or two from our below itinerary.

 

Day 1 : Drive into Vermont. Dinner at Von Trapp Brewing and Overnight stay at Trapp Family Lodge

Day 2: Explore Stowe (lunch, shopping, Alchemist Brewery, Ben & Jerrys) and take tours and lessons at Trapp Family Lodge

Day 3 : Check out of Trapp Family Lodge, Baird Family Farm, Arrive at Mountain Top Resort, snowshoe, sleighride and dinner

Day 4: Ski lessons at Mountain Top Resort and spa day. Maybe drive out to Vermont Country Store or Greenbrier Gift Shop.

Day 5 : Check out of Mountain Top Resort, explore Rutland, check into Killington Resort

Day 6 : Ski Lessons at Killington, pool, local nightlife

Day 7 : Day trip to Manchester and depart

 

7 day Vermont Itinerary

learning to ski at 40

 

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