Moonlight in VermontPhoto courtesy of Kiera Slye Photography

For the past six years, my husband and I have made a tradition of taking a trip for New Year’s. Really it started more than a decade ago, the year we started dating. We drove from Texas to New York City to ring in 2004 and we stood in Times Square for six hours in sub-freezing temperatures to watch the ball drop from eight blocks away. We’d never been to New York before and had no concept of the lay of the land, so we naïvely booked a hotel on the New Jersey side of the George Washington Bridge. Do you know how hard it is to get a cab to take you to New Jersey at 1 a.m. on New Year’s?

Since then we’ve become infinitely more savvy travelers, and our subsequent New Year’s trips have gotten better and better:

  • 2010: Italy
  • 2011: Spain and France
  • 2012: Switzerland
  • 2013: Estes Park, Colorado and Jackson Hole, Wyoming
  • 2014: Crested Butte, Colorado

This year we mulled over several destinations and eventually decided to split our time between New England and New York. We would fly into Boston, drive up to Vermont and spend two days in Woodstock, then we’d take the train from Boston to New York and spend New Year’s Eve in the city (not in Times Square this time, and we wouldn’t be staying in New Jersey).

We left on an inhumanely early flight on a Sunday morning and landed in Boston around 10 a.m. Two of our Boston friends were planning on meeting up with us in Vermont later on in the day, so we had some time to meander our way north. I decided to drag Michael to one of my favorite places in the world, the Montague Bookmill, a small used book shop in the tiniest of towns in western Massachusetts.

Montague Bookmill

I’d read about the Montague Bookmill long before I ever visited it. It’s always showing up on Buzzfeed-y type lists like, “10 Bookstores You Must Visit Before You Die.” A little over two years ago, I took my mom on a trip to New England to celebrate her 60th birthday and I made the Bookmill one of our pit stops. I immediately fell in love. I went a second time when I was in Boston for work the summer before last. I bought a lovingly worn copy of The Garden of Eden, ordered a salad and a Chimay at the Lady Killigrew Café, which is attached to the bookstore, and and enjoyed a sunny summer afternoon at one of the outdoor tables overlooking the Sawmill River.

Montague Bookmill

Books are to Michael what . . . I’m trying to find the proper analogy . . . socket wrenches are to me. So he was a great sport for hiking out to middle-of-nowhere Massachusetts with me just so I could go to the Bookmill, but I think he ended up enjoying it. We got there around noon and, after I gave Michael a brief tour of the shop’s many enchanting nooks, we ordered lunch at the Lady Killigrew and were somehow lucky enough to nab a table by the window. My favorite little detail? There were small signs posted on several of the tables that said the café would be a “laptop-free zone” from 11 a.m. until 4 p.m. Sit. Eat. Sip. Read. I love it.

Next it was onto Vermont. We were staying at the Kedron Valley Inn in South Woodstock, Vermont, which is essentially a straight shot north from Montague. We hadn’t seen any snow on the ground in Massachusetts, which rather killed my Bing Crosby-esque daydreams of a holiday in New England, but as we drove deeper into Vermont, the white stuff started showing up here and there. By the time we got to South Woodstock, we were in a winter wonderland, complete with wreath-clad covered bridges and red barns dripping with icicles.

South Woodstock VermontWe got to the inn just before sunset and our room was cozy and inviting—exactly what you’d expect from a Vermont bed and breakfast. As we were unpacking, our friends knocked on our door and we made grand plans for the night: wine in their room, and then dinner at the inn’s restaurant.

Kedron Valley InnOur friends, Frank and Kiera, went to law school with Michael and they are two of my favorite people in the world. Frank is equal parts fun-loving and hard-working, and he’s the sort of person about whom no one could possibly have a bad thing to say. Kiera has a smile that stays with you the way the sun stays in your eyes when you look at it for a beat too long. Her happiness is infectious and you just can’t be sad when you’re around her. As if her sparkling personality weren’t enough, she’s also a terribly talented photographer (she took the starlit photo at the top of this post—hell no, I could not have taken that myself!) and she recently helped launch she., an inspiring initiative aimed at empowering women and breaking stereotypes. In short, she’s the bee’s knees.

Oh and also, they have a magical dog named Cody. He is adorable, and I wish we lived closer so I could smoosh his face on a daily basis. Here he is eating a snowman’s nose:

Cody Pup in Woodstock, VermontAnyway, enough bragging about how awesome my friends and their pets are.

We tore through a bottle or two of wine in Frank and Kiera’s room and caught up on the past year. They were married last April and we hadn’t seen them since the wedding. Sufficiently lubricated, we walked over to the inn’s restaurant where we ordered another bottle of wine (YOLO) and enjoyed some delectable Vermont-grown fare. The dining room was dimly lit and equestrian themed—which is to say, I loved every last inch of it.

Kedron Valley InnAfter dinner, all four of us were feeling travel weary, so we parted ways and slept the deep and glorious sleep that only a belly full of wine and delicious food can elicit.

The next morning we woke up early and met up in the inn’s breakfast room. Breakfast is one of the best things about staying at Kedron Valley Inn. They have all the usual suspects like coffee, juice, toast and bagels, yogurt and granola, as well as freshly prepared eggs, French toast, and bacon—from a farm in New Hampshire, no less! I don’t eat meat, but I have a lot of appreciation for places that make an effort to know where the food they’re serving comes from.

After breakfast, Michael and our friends headed off to Killington to go skiing for the day. There is nowhere I look less graceful than on the slopes, so I volunteered to stay at the inn with Cody pup. We had a phenomenal day.

Kedron Valley InnOnce the crew got back from a frigid day of skiing, we drove into Woodstock to take Cody for a proper walk and to explore the town a bit. Woodstock looks like it was designed specifically for Christmas. Every house and shop was trimmed with pine garlands and red bows, and inviting smoke was drifting out of every chimney. And we of course took a few requisite shots in front of a covered bridge.

Woodstock, Vermont

After strolling through Woodstock in the cold, we couldn’t move our appendages, but it was too early to stop for dinner so we drove back to the inn for—you guessed it—some pre-dinner wine and conversation and giggles. Kiera and I made bold and hopeful plans for extravagant adventures in the year to come, and Frank and Michael discussed . . . I don’t know . . . whatever it is that boys talk about when their wives are three-quarters of the way through a bottle of sauvignon blanc.

We eventually ventured back out into the cold in search of sustenance and ended up at Bentley’s, a charming pub-type restaurant with standard American offerings and a totally decent beer selection. We all ordered burgers (I, a veggie burger) and beer (natch), but the best and most memorable part was a bit of banter we had with our waiter.

MICHAEL: What’s the soup du jour?

COOLEST WAITER IN THE WORLD: It’s the soup of the day.

Best. Ever.

After we got back to the inn, Michael and I went to our room and fell asleep, while Kiera went out in the cold and took some incredible night shots (as evidenced above). We got up early again the next morning and enjoyed yet another delectable Vermont breakfast, after which we reluctantly drove to Boston and parted ways with our dear friends before hopping on the train to New York for the next leg of our trip . . .

Train to New York