Girls’ Ski Weekend in Killington, Vermont: A 3-Day Itinerary

Flying over Vermont in a Cape Air six-passenger plane, as the sun began to set, I knew this weekend was going to be an adventure. From my window, I watched the sky change from soft blue to shades of pink, orange, and yellow as we descended down into Rutland, Vermont.

I think we were all trying to distract ourselves from how small this plane was and how we could see the pilot’s every move. 😂 The ride was smooth and it was honestly so cool to ride in a plane that only fit seven passengers. Our crew took up the majority of the plane, and we made friends with the other three ladies on our flight too!

We landed at the smallest (but cutest) airport I had ever seen, Rutland Southern Vermont Regional Airport, collected our luggage, and set off for the mountains. And just like that, our girls’ ski weekend had begun.

For my birthday, a group of girlfriends and I decided to spend a long weekend skiing in Killington, Vermont. None of us had visited before, and between the tiny plane, snowy mountain roads, and figuring out how to navigate a new ski town, every part of the trip felt like an adventure.

Over three nights, we skied Killington Mountain, took the gondola to the summit, discovered some wonderful restaurants, and experienced the town’s lively après-ski scene. There were beautiful mountain views, freezing temperatures, live music, plenty of laughter, and a few unexpected moments along the way.

If you’re planning a winter getaway, here’s how we spent our girls’ ski weekend in Killington, including where we stayed, our favorite restaurants, how we got around, and what I would do differently next time.

Getting to Killington, Vermont

We flew from Richmond, Virginia, to Boston on JetBlue before connecting to Rutland, Vermont, on Cape Air. Flying into Rutland was incredibly convenient, as the airport is only about a 30-minute drive from Killington Resort.

Cape Air operates small regional aircraft, so the experience is quite different from flying on a traditional commercial airline. With limited luggage space, I recommend checking the airline’s baggage requirements before packing, especially if you’re traveling with ski gear.

Once we landed in Rutland, we were picked up by The Mountain G.O.A.T., a local transportation company offering private and group shuttle services throughout the Killington area.

Before heading to our condo, we made a quick stop at Hannaford grocery store in Rutland to pick up breakfast essentials, snacks, wine, and frozen pizzas for dinner. Having groceries on hand made our mornings much easier, especially with two full days of skiing ahead.

Getting Around Killington

One thing I would recommend planning ahead is transportation. We decided not to rent a car for this trip, which was manageable, but required a little coordination.

In addition to The Mountain G.O.A.T., we used Green Mountain Cab throughout the weekend. The owner, Jeremy, was incredibly helpful and arranged rides between our condo, ski rentals, the mountain, and the airport.

Killington also has a public bus system, which we used once to get to the resort. I recommend checking the local transit schedules before your trip, as routes and operating hours vary.

Another convenient option is the complimentary shuttle service offered by certain restaurants and nightlife destinations. We took advantage of these services for Wobbly Barn, The Foundry, and Pickle Barrel. We simply called ahead, left a voicemail requesting transportation, and received a callback confirming our pickup time. Although our rides were complimentary, tips for the drivers were appreciated.

My advice: If you’re visiting Killington with a group, consider renting a car for added flexibility. While we successfully navigated the weekend without one, having our own transportation would have made grocery runs, ski rentals, and exploring the area a little easier.

If you’re flying, I would also compare flights into Burlington, Vermont, or Albany, New York, and consider renting a car from either airport. Both are alternatives worth exploring depending on where you’re traveling from.

Where We Stayed: Whiffletree Condominiums

For our three-night stay, we booked Whiffletree Condo Unit I3, located just a short distance from Killington Resort. I brought all the girls a protein bar and a fireball shot for a little breakfast and pick-me-up for the slopes the next morning!

Traveling with a group, we loved having a condo where everyone could spread out, relax, and enjoy time together after a full day on the mountain. Having a kitchen was especially convenient for preparing breakfast before skiing and keeping snacks and drinks on hand throughout the weekend.

After arriving Thursday evening, we unpacked our bags, made frozen pizzas, poured a few glasses of wine, and settled in for a cozy night. With two full days of skiing ahead of us, staying in was exactly what we needed.

Whiffletree’s location made it a convenient home base for accessing the mountain. The property also offers ski shuttle service on select days during the winter season, although we relied on a combination of local taxis and public transportation throughout our stay.

While we enjoyed our accommodations, one thing I would consider for a future visit is staying closer to Killington Road, where many of the area’s restaurants, bars, and other attractions are located. Without a rental car, having more destinations nearby would have made getting around a little easier.

My recommendation: If you’re visiting Killington with a group of friends, renting a condo is a wonderful option, particularly if you want a shared space to relax between ski days. Just be mindful of the location and transportation options when booking, especially if you don’t plan to have a car.

Day 1: Skiing Killington Mountain & Dinner at Wobbly Barn

Friday morning, we woke up early, made breakfast at the condo, and headed out for our first full day on the mountain. We couldn’t have asked for better weather. The sun was shining, the slopes were beautiful, and we were all excited to finally experience Killington.

Skiing at Killington Resort

Killington Resort is one of the largest ski resorts in the eastern United States, offering an extensive network of trails for skiers and snowboarders of all experience levels.

Kate and Brooke booked a morning lesson while the rest of us headed out to explore the mountain. One unexpected bonus was that their lesson package included two complimentary lift tickets, which they were able to share with us. If you’re traveling with beginners, it’s worth checking the available lesson packages and promotions before purchasing everyone’s lift tickets separately.

For ski rentals, we visited Northern Ski Works, a local ski shop near the resort. I recommend reserving your equipment ahead of time and allowing extra time on your first morning for fittings and pickup.

Once everyone was ready, we spent nearly the entire day skiing, exploring different trails, and taking in the beautiful Vermont scenery.

Lunch at the Peak Lodge

One of my favorite experiences of the weekend was riding the K-1 Gondola to the top of Killington Peak.

At the summit, you’ll find the Peak Lodge, where you can warm up, enjoy lunch, and take in panoramic views of the surrounding mountains. We stopped for Reuben sandwiches and burgers, and the views alone made it worth the visit.

Whether you’re spending the entire day skiing or simply want to experience the mountain from above, I highly recommend making time for the gondola. It’s one of those experiences that really captures the beauty of Vermont in winter.

And of course, after lunch, we headed back out for a few more runs! Our favorite trail of the trip ended up being a long blue run that started at the top of Killington Peak and took us all the way down the mountain. It had just the right amount of challenge while still being really fun, with winding sections, beautiful scenery, and even a few opportunities to weave between trees.

Friday Night: Dinner, Drinks & Dancing at Wobbly Barn

After skiing all afternoon, we headed back to the condo, turned on the fireplace, made some coffee, and warmed up before getting ready for our first night out.

Our destination was Wobbly Barn, one of Killington’s best-known restaurants and nightlife spots. The property has a steakhouse downstairs and a lively nightclub upstairs, complete with live music and dancing.

We spent the evening enjoying dinner, drinks, and music, and it was exactly the kind of atmosphere we had hoped to find on a girls’ ski weekend.

Also, there was a photobooth which we took full advantage of!

One of the best parts was not having to worry about transportation. We arranged a complimentary shuttle to pick us up from our condo and bring us to Wobbly Barn, making the evening easy and convenient.

If you’re planning a weekend in Killington and enjoy live music, Wobbly Barn is definitely worth adding to your itinerary. It’s a classic ski-town experience and a fun way to end a day on the slopes.

Day 2: More Skiing, Mountain Views & Birthday Celebrations

Saturday morning brought an entirely different kind of weather. After enjoying beautiful conditions on Friday, we woke up to bitterly cold temperatures. Nevertheless, we bundled up and headed back to Killington for our second day on the slopes.

We managed to get a few runs in before deciding it was time to escape the cold and warm up!e

Back on the K-1 Gondola to Peak Lodge

We made our way to the K-1 Gondola for another trip to the summit. Even though we had visited the day before, the mountain views were so beautiful, we wanted to go back for a second time around to warm up with drinks and lunch. Kate and Brooke joined us in the lodge this time which was a special treat! They warmed up with some mulled wine waiting for us to join them from the cold!

Once we made it to the top, we all settled into the lodge for warm drinks and bowls of chili, which tasted especially good after spending the morning in the freezing temperatures. Between the sweeping views and the chance to warm up, it served as a cozy place for us all to catch our breath and warm up!

After lunch, our group split up for the afternoon. Kate and Brooke headed off to try snow tubing, while Caitlin, Camille and I, continued skiing. Eventually, the cold got the best of us, and we decided to head back to the condo a little earlier than planned.

Birthday Dinner at The Foundry at Summit Pond

That evening, we made our way to The Foundry at Summit Pond for my birthday dinner. Of all the restaurants we visited during our weekend, this one was very nice and elevated and the perfect spot for a nice dinner and celebration.

The Foundry has a beautiful, cozy atmosphere that feels perfectly suited to a Vermont winter evening. We hadn’t made a reservation, and when we arrived, we were told there would be about an hour wait.

Luckily, the restaurant has a wonderful bar area, so we ordered a bottle of red wine, found a place to sit, and spent the next hour catching up while listening to live music. It was such a lovely way to begin the evening that we hardly minded waiting.

And dinner was well worth it.

We started with bread served with maple butter and shared several dishes around the table, including the restaurant’s famous macaroni and cheese, steak frites, arugula salads, and pumpkin butternut squash ravioli. Everything was delicious, but the maple butter was particularly memorable.

To make the evening even sweeter, our waiter surprised us with three desserts for my birthday: berry cheesecake, lemon layer cake, and crème brûlée. Naturally, we tried all three!

Between the food, atmosphere, and thoughtful birthday surprise, The Foundry was a highlight of our weekend.

If you’re planning a special dinner in Killington, I couldn’t recommend it more. Just be sure to make a reservation in advance, particularly if you’re visiting on a weekend during ski season.

Saturday Night at Pickle Barrel

After dinner, we took the shuttle over to Pickle Barrel Nightclub, one of Killington’s most popular nightlife destinations.

We had heard so much about Pickle Barrel before our trip that we knew we wanted to experience it at least once.

There was a $30 cover charge the night we visited, which felt a little steep, but we figured we were only in Vermont for the weekend!

Inside, the nightclub spans multiple levels, with several bars, live bands, and plenty of dancing. A band was performing on the main floor, while additional music and bars could be found upstairs.

It was lively, energetic, and a fun way to end our last full evening in Killington.

If you’re planning a girls’ ski weekend and enjoy live music and dancing, I would definitely add Pickle Barrel to your list. It’s a quintessential Killington nightlife experience and a memorable way to wrap up a weekend on the mountain.

Day 3: Heading Home

Sunday morning came bright and early as we packed our bags and prepared for our flight home. We arranged transportation back to Rutland Airport with Green Mountain Cab before boarding our Cape Air flight to Boston and connecting to Richmond. Again, distracting ourselves on the Cape Air flight with a little window condensation tic-tac-toe.

After three nights, two days on the mountain, and plenty of memorable meals and adventures, our girls’ ski weekend had officially come to an end.

What I Would Do Differently Next Time

While we had an incredible weekend in Killington, there are a few things I would consider for a future trip:

• Rent a car: Although we managed without one, having our own transportation would have made getting to the mountain, restaurants, and grocery stores much easier.
• Explore other airports: Flying Cape Air into Rutland was an unforgettable experience, but I would also compare flights into Burlington or Albany and consider renting a car from there. Next time I visit Killington, I will probably fly into Burlington. I have heard that town is very quaint and has nice shops and restaurants and would be fun to explore as an added bonus place to your ski trip! 
• Stay closer to Killington Road: If traveling without a car, I would look for accommodations closer to the main road for easier access to restaurants, nightlife, and public transportation.
• Make dinner reservations: Especially during ski season! We lucked out at The Foundry, but booking ahead would make evenings a little more seamless.

Until Next Time, Killington

Looking back, I think what made this weekend so memorable was that none of us had ever been to Killington before. From boarding that tiny Cape Air plane and landing at the smallest airport I’d ever seen to navigating a new mountain, discovering local restaurants, and dancing the night away, every part of the trip felt like an adventure.

And that’s one of my favorite things about traveling with friends. You don’t always need a perfectly planned itinerary or a familiar destination. Sometimes the best memories come from choosing somewhere new, figuring things out together, and enjoying everything that comes along with it.

Killington gave us beautiful mountain views, wonderful food, plenty of skiing, and a birthday weekend I’ll always remember. ❆⛄︎

If you’ve visited Killington before, I’d love to hear your favorite places to stay, ski, and eat. Leave your recommendations in the comments below!

We love you, Killington!! Be back soon.

Read, Watch, Listen: Vermont Edition

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