In July 2018, on the eve of our second wedding anniversary, Ian told me he was whisking me away for a weekend. The destination, he said, was a surprise.
I was thrilled — I love a well planned surprise, especially when it involves exploring beautiful New England in my favorite season with my favorite person.
(That said — have you ever tried packing for a trip to an undisclosed location? I’m here to tell you it ain’t easy.)
When we hit the road on Friday evening, I started narrowing down possible destinations in my head. I thought we might be headed to the Berkshires, which in the summer boasts not only natural beauty but also world-class culture: think classical music at Tanglewood and contemporary art at Mass MoCA. I also considered the possibility that we were on our way to the Hudson Valley, home of magnificent wineries, charming sleepy towns and an NYC-caliber restaurant scene.
But I was most convinced we were bound for Vermont, a state we both couldn’t wait to visit. On paper, Vermont seemed like exactly our kind of place: it had crunchy hippie roots, beautiful mountain scenery, a plethora of outdoor activity possibilities, and most importantly a lot of maple syrup and cheese.
As we crossed into the southeastern corner of Vermont — suspicion confirmed! — I was excited to see if the state would measure up to my Mt. Mansfield-high expectations.
Folks, it was love at first sight — literally. Within the first half hour, we hit this magnificent viewpoint:
All at once, I realized why winter in Rhode Island felt so lackluster and why I missed Boulder so dang much: Because Rhode Island is as flat as a pancake! This was the first time I’d seen a mountain vista in six months. It was glorious.
As dusk descended, we pulled into the adorable town of Wilmington, where we’d be based for the next two days. “Town” is perhaps a generous descriptor of pint-sized Wilmington — it’s really not much more than a half-mile stretch of highway with a handful of restaurants, shops and adventure outfitters. Yet it has everything a discerning weekender could possibly want, including great food, an impressive roster of concerts and shows, and an amazing variety of handmade gifts to take home. Most importantly, it’s got that New England je-ne-sais-quoi about it — that woodsy, cozy quaintness I wasn’t sure existed beyond the pages of Yankee Magazine.
After dropping our luggage inside the adorable Airbnb, Ian and I walked “across town” (read: two blocks away) for an uncharacteristically lavish dinner at Cask & Kiln, a relatively new restaurant housed in a historic brick building that had been ravaged by river flooding caused by Hurricane Irene in 2011. This place is as much about romantic atmosphere as it is about food, all low lights and leather tufted seats and Art Deco details. I loved that everything about the restaurant, including the decor, the menu and even the outfits of the servers, managed to feel at once contemporary and nostalgic, simultaneously casual and celebratory. The least classy thing about the place? Us — we had mostly packed outdoor adventure clothes and were easily the most underdressed people there!
The next morning, I woke up early to get the lay of the land. With a cup of coffee in one hand and a blanket around my shoulders, I read up on the area’s parks, attractions and seasonal events and consulted a map of the area. Soon I was fired up for a day of scenic hiking, kayaking, farmer’s markets and covered bridge peeping (it’s a real hobby!) — and I was already plotting return trips in the fall and winter, when the area appears equally gorgeous.
We kicked off Saturday morning with a Cajun-inspired breakfast at Jezebel’s Eatery and a brief tour through some of the town shops. Sometimes I feel like the same 50 books are on display in every bookstore, so I was pleasantly surprised by the eclectic and locally-focused displays at Bartleby’s Books. I think our visit here inspired about half of my holiday gifts in 2018!
After grabbing some local honey at a farmer’s market on the outskirts of town, we pulled into Molly Stark State Park — where we were stunned to discover we were one of just a handful of visitors that morning. After consulting a ranger and a trail map, we followed signs to the Mt. Olga Fire Tower, which promised sweeping views of the Green Mountains. Promise delivered.
One thing I love about New England is its plethora of easy and moderate hikes. Many people who live in the West, particularly those in Colorado, approach hiking with a “no pain, no gain” philosophy and believe the best views can only be found by enduring grueling climbs. This 1.7-mile jaunt proves all those hiking snobs wrong.
After Molly Stark, we reversed course, heading west on the state’s main southern highway with no particular destination in mind. Google Maps first led us to Woodford State Park, where we found a few-mile trail circumnavigating Adams Reservoir. Some families were paddling their kayaks and canoes on the calm waters, and we dreamed of returning here in the fall to do the same.
After relaxing for a while at the reservoir’s picnic area, we continued west and grabbed lunch at a bohemian coffee shop in Bennington. Wondering where to go next, we pored over the local tourism guides for inspiration. Almost immediately, we zeroed in on Bennington College — the alma mater of several big literary names, including Donna Tartt. We’d both recently read “The Secret History,” which was based on her time there, and we were intrigued to see if the place felt as mysterious as it had been portrayed in her novel.
The campus was beautiful, austere and almost disturbingly quiet in the middle of summer. We spent a pleasant couple of hours imagining spots where Tartt’s characters might have held their bacchanal or crossed the quad for Greek lessons.
Back in Wilmington, we hit up Red Fox Shop, a local wine, cheese and gift store, to assemble our own ploughman’s dinner. The place was so unexpectedly delightful that we stayed almost an hour chatting with the owner, browsing funky cheeses and shopping for gifts. Then, we took our finds back to the Airbnb and lounged on the riverbank until the mosquitoes chased us inside.
On Sunday morning, we weren’t quite ready to return to the real world — so we took the scenic route home. Our first stop was a charming covered bridge near Brattleboro, the first one I’d ever seen on the East Coast.
After crossing into Massachusetts, Ian suddenly remembered one of his favorite area destinations from a previous trip here. Drawing largely from memory, he navigated us to the Montague Bookmill, a former 19th-century grist mill that is now home to a sprawling complex of used books, cafes, food stalls and local artists’ pop-up shops.
We had another three hours of driving ahead of us, otherwise I might have spent the entire day here. I loved everything about this spot — the sun-soaked reading nooks, the unpretentious vibe, the vibrant art, the friendly and talkative people.
Needless to say, this weekend confirmed my assumptions that I’d love Vermont. Despite never having visited before, the Green Mountain State felt familiar to me. Maybe it’s because Vermonters seem so much like Santa Cruzans, filled to the brim with local pride and refreshingly far removed from the career-focused hustle of the I-95 corridor. Or maybe it’s that they spend so much more of their time outside, even in the depths of winter, like in our previous home of Boulder. Whatever it was, I know one thing: I’ll be back soon.