Meandering Vermont Road Trip

When Emily and I left Boston on Tuesday afternoon, it was 70 degrees and balmy. It felt weird to pack our skis, insulated jackets, mud season boots, and cozy slippers. We were off for a last-minute Vermont vacation – without much of a plan other than we would crash with friends, ski/ride, and see where the roads would take us.

Lebanon, NH, Hanover, NH, and Quechee, VT

Our first night we crashed with our friend Kathy in Lebanon. She’s teaching at Dartmouth these days and brought us to The Mill at Simon Pearce, part restaurant, part glassblowing factory, part showroom. We had dinner right above a roaring dam!

The next morning we grabbed breakfast at Lou’s, a popular Dartmouth diner. Great food, awesome service. After touring Kathy’s academic building and almost crashing her office hours, Emily and I headed on our way.

Quechee, Woodstock, and Bridgewater

This was easily the most touristy stretch of our road trip. Lots of little stops along the way, starting with a picturesque view of Quechee Gorge. Then, the Quechee Antique Mall where we met some alpacas and hundreds upon hundreds of antique stands. The mall was a bit of a tourist trap… so we got out of there in 15 minutes flat.

Quechee Gorge

The highlight of the afternoon was our spontaneous stop at the Vermont Institute of Natural Science Raptor Center, where we saw hawks, eagles, vultures, falcons, owls and ravens – all were all rescued and rehabilitating from hunting or vehicular accidents. We got there just in time for their daily feeding, which meant we met lots of the staff and learned about each bird.

We ended the afternoon with a luxurious stop at Worthy Kitchen, where we demolished some excellent donuts (really, they were beignets) and a quick stop at Long Trail Brewing (where we decided we weren’t into their style of beer).

Ludlow, Okemo, and Homestyle Hostel

That night, we crashed at Homestyle Hostel, which I’ve previously called “The Best Hostel I’ve Ever Stayed At.” We met up with our friend Stephanie and headed to The Downtown Grocery for dinner. We ended up sitting at the bar and hanging out with the bartender for a few hours. They were fantastic. Great food and drink. We ended up sampling one of the cocktails she was making, “Purple Haze…” see below for a list of ingredients.

It was a perfect girls’ night out, and that night we returned to Homestyle Hostel to crash. I was staying in the dorm-style bunks which had 6 beds, and was sound asleep by about 11:30 p.m. Around 1 a.m I woke up to the sound (and smell) of a very drunk guy stumbling back. He spent about half an hour on the phone having a meltdown about his friend, while flipping the lights on and off and pacing back and forth by my bunk. I waited until he went to the bathroom and snuck out upstairs to crash with Em and Steph (we were separated becacuse they didn’t have enough rooms upstairs). We finally went to bed around 2 a.m., but then Steph and I were both woken up again by the guy (very poorly) playing guitar in the living room. It was such an unusual experience for the Homestyle Hostel… I’ll circle back to how the hostel handled this the next day.

Early the next morning, Steph, Em, and I hit the slopes at Okemo Mountain Resort, after a quick gear stop at The Totem Pole. The hostel was 5 minutes away from the base lodge, so we were there right when lifts opened. While the morning started off with scratchy runs and hardpack, we ended up getting a few inches of snow in the afternoon. By the end of the day, the runs were soft and fast. I couldn’t have been more pleased. Also, as someone who skis Sunday River and Sugarloaf in Maine often… it was mind-blowing to sit on a heated chair lift, have on-mountain sit-down dining, and RFID passes. As someone told me at the hostel, “The Maine ski hills are like going back to the 90s.”

When we got back to the hostel, we ran into Eliza and Justin, the owners of Homestyle Hostel. I explained to Eliza what happened and she immediately apologized, refunded our night, asked the drunk (now hungover) guy to leave, and changed the door codes. I was impressed with how she handled everything so speedily and professionally. The rest of our stay was awesome.

That night, we had an amazing dinner at the hostel. Since my last stay there in 2015, they opened a restaurant in the downstairs area four nights a week (Thursday through Sunday). The cocktails were incredible, and the meal was one of the best I’ve had in months.

The next morning we meandered to breakfast and chilled out in the hostel’s beautiful cozy downstairs space.

Killington to Randolph

This day was all about taking our time driving north. We picked random roads and stopped at random places. It helped that (other) Steph had spent plenty of time in Vermont, so she had great recommendations along the way.


On our last day, we did a whirlwind tour of Stowe, VT.

  • Scoops at Ben & Jerry’s Factory, and visited the flavor cemetary.
  • Samples at Cabot Cheese.
  • Sips at Smuggler’s Notch distillery.
  • Apple cider donuts at Cold Hollow Cider Mill.
  • Heady Topper and Focal Banger at The Alchemist. The brewery only had men’s t-shirt sizes in their merch store – such a bummer for a girls’ trip.
  • Trapp Family Lodge and Brewing. Definitely sang a few songs in the car.
  • Dinner at The Blue Stone.

For a spontaneous, last-minute trip, Vermont was ideal. There was so much to do, and we could do it all at our own pace. If we’d had more time, we would have made it up to Burlington and maybe even Montreal. But for a few days over school vacation week, this was just about perfect.

A rough map of our route.