Traveling With Kids: Woodstock, Vermont

This summer has been really, really crazy. Quite frankly, it hasn’t felt much like summer, save the mental Olympics required to remember which kid is going where and at what time. I suppose this is just what happens when you have two parents who are self-employed and subsequently don’t take a lot of time off. I mean, I’m super grateful for the life we’re living AND Jon and the girls and I have been in desperate need of R&R together.

Subsequently, I was delighted to be invited by the Town of Woodstock, Vermont to visit and explore with my travel writer hat on. Traveling with kids has always been really important to me -- partly because I really need to leave home to truly unwind, partly because I’m a major proponent of experiences instead of things (especially with kids because OMG experiences don’t create clutter!), and partly because time and again we’ve experienced that there’s something a bit magical that happens when you’re exploring as a family together, all on the same unknown footing.

So let’s talk about Woodstock, Vermont! Woodstock is just under two and a quarter hours from Boston, totally doable with kids even sans devices (which is how we need to roll since Laurel and Violet both get carsick with books or devices in the car). We spent most of our time in the village (center of Woodstock), and other attractions we explored were all pretty much within a one-mile radius. We arrived on Friday evening and left late Sunday morning and absolutely could have spent many more days. Here’s what we explored and enjoyed during our visit -- following the trajectory of lodgings, attractions, food, and shopping:

1. Woodstock Inn & Resort

The Woodstock Inn & Resort touts itself as “Vermont’s most beautiful address” and they very well may be right. This property is tucked back quietly off the main green but is actually quite expansive, offering pretty much everything you need, such as a variety of excellent dining options (including what Jon proclaimed was the best buffet breakfast he’s ever experienced, at The Red Rooster), a spa (more on that in a second), a gift store, outdoor pool (it wasn’t easy convincing Laurel and Violet out of there!), game room, and a variety of recreation options and events through the week. The property also offers access to the Woodstock Athletic Club, Woodstock Country Club, New England Falconry (more on that in a second), and its own Suicide Six ski area (which I’m already thinking about checking out this winter) and Nordic Center. You could easily book a week’s stay at the Woodstock Inn & Resort and have plenty of time to both relax and be active through their offerings. Also, yes, the hotel is perfectly suited for families, but I immediately started fantasizing about returning there with Jon for a retreat, or for a girlfriend getaway!

I managed to get a last-minute appointment at The Spa at the Woodstock Inn & Resort and, well, WOW. Whereas the hotel itself is elegant and traditional in design, the LEED-certified spa has a modern, minimalist aesthetic perfect for instilling an immediate sense of calm. The spa offers massage and body treatments, skin care, and salon services and is well appointed with amenities and plenty of indoor and outdoor spaces to relax. I will say that I am super picky about massage; I have had many massages to deal with different physical issues and my massage therapist Sara did not disappoint! She provided a fantastic deep tissue massage, preceded by a citrus espresso body treatment. I was so relaxed afterwards that I threw my actual shoes in the spa slipper return basket.

So here’s a thing about my family and me on vacation: we typically like to play it fast and loose and not be bound by appointments. However, as soon as I heard about the New England Falconry I had a feeling we needed to book a visit. Birds of prey are Jon’s spirit animal, and I also really value getting my city kids up close and personal with animals. The experience was truly magical and perhaps a little mystical for all of us. We had a session with Gregory, an incredibly smart and friendly falconer, and he introduced us to a variety of birds (Violet met two owls...mind = blown!) and then Jon, Laurel, and I had several opportunities each to have Newton the hawk land on us. It was CRAZY AWESOME. Laurel said it was the most amazing thing she’s ever done in her life.

4. Billings Farm & Museum

And speaking of animals, I took the girls to the Billings Farm & Museum to visit the cows and sheep. We missed the formal weekend programming (note previous play-it-fast-and-loose issue), but it was a nice, relaxed opportunity to get my city kids on a farm.  

5. Kedron Brook

So this is not exactly an attraction, but Kedron Brook runs through the town center (you can access it via stairs on Central Street between R. T. Home and Collective - The Art of Craft). I’m not sure if the water is usually that low, but it was a beautiful, rocky, super shallow brook where the girls spent a happy hour hopping from stone to stone and making up games while I did not need to panic about anyone falling in deep water. Instead, I could take pretty cairn pictures. Ha.

6. Hiking

Just before we departed on Sunday, we visited Faulkner/Billings Parks. We didn’t have time to hike but this is something I’d like to return to do. Faulkner Park is right off Mountain Avenue and has a series of paved pathways perfect for Violet to zip around on her kick bike. We walked into the entrance of Billings Park and I would love to do the Faulkner Trail to Mount Tom’s South Peak, which looks like it would be doable with the kids. There are also tons more hiking opportunities via Marsh - Billings - Rockefeller National Park.

Situated right in the center of Woodstock Village, we landed twice at Bentleys Restaurant during our trip. On Friday, we ate an early dinner on the road and after arriving and getting settled at the Inn, we popped in to Bentleys for snacks. We also had dinner there Sunday night. Bentleys is great for families in that they offer an affordable kids menu, tasty standards (give me ALL THE ONION RINGS), and items for the more evolved palette, such as the bacon wrapped scallops, mushroom gnocchi, crab cakes, and filet mignon (#nomnom). I’d also be hard pressed to turn down their delicious elderfashion cocktail if someone handed me one right now.

8. Mon Vert Cafe

Mon Vert Cafe welcomes visitors with a “Come In, We’re Awesome” sign and that’s a pretty accurate welcome. Jon popped in three times over the weekend! The cafe offers tasty food as well as killer baked treats and coffee. I highly recommend 10 pieces of the classic coffee cake.

9. Ice cream

It’s totally on point for me to make two ice cream recommendations. I love ice cream! I used to scoop ice cream for a living! Mountain Creamery is right on Central Street in the village. I have never had breakfast or lunch there but the ice cream is solid. The White Cottage Snack Bar is just over a mile outside of the village and offers classic casual fare and also ice cream servings the size of your head. If you’re thinking of being demure and ordering a kid sized serving, forget about it -- I did that and received a small the size of my head. White Cottage also has the added bonus of being siutated along the Ottauquechee River -- we had an amazing view while eating our giant ice creams.  

10. Shopping

I always love browsing and supporting the local indie economy when I travel! We had fun browsing and shopping at F. H. Gillingham & Sons (a classic general store), R. T. Home (home goods, with an interesting mix of classic pieces as well as items from Africa), Red Wagon Toy Company (where we bought Violet an awesome pair of water sandals -- perfect timing since she had blown out one of her other pairs), The Village Butcher (an old style butchery), Yankee Bookshop (yay, books!), and Clover Gift Shop (where Laurel found Violet the most adorable little owl necklace + owl case...for a mere $7.95!).

What’s Next?

Man, that sounds like a lot -- and I guess we did, in fact, squeeze in a lot -- but I still feel as if I just scratched the surface. I’m eager to return to Woodstock to explore further, and I won’t lie, after I got home I browsed Woodstock properties on Zillow! There are several food/shopping stops (e.g., Woodstock Farmer’s Market, Farmhouse Pottery, Worthy Kitchen) we just didn’t have time for, I’d like to photograph the other area covered bridges (I’m a little obsessed with covered bridges), and would love to try some of the day hikes and bicycle rides starting from the Town Green. We also didn’t even have a chance to look at any of the art and craft galleries, and I want to do a little trip into neighboring Quechee (I’m both intrigued and terrified by the gorge!), including checking out the Vermont Institute of Natural Science.

In a nutshell, if you’re looking for a beautiful, family-friendly respite in close striking distance to Boston, visit Woodstock, Vermont. And I highly recommend booking at the Woodstock Inn & Resort in order to have a really phenomenal home base from which to launch your active and relaxed vacation pursuits!

Disclosure: The Town of Woodstock kindly hosted my family while I explored the property for editorial consideration. All opinions and experiences are, of course, my own.