At All Roads North, we believe that a place is nothing without its people. So often, when we ask our clients the most memorable parts of their journey, it’s not the Instagram-worthy landscape or acclaimed hotel that they mention, it’s the encounters they had along the way.  That’s why our trips are carefully designed to make those connections, providing you with an authentic and immersive experience. These experiences– whether it be with a local craftsman, musician, chef or marine biologist– are the inspiration for our Connections series, where we talk to friends of All Roads North to get an insider’s look at some of our favorite places across the U.S.

Tell us about your Woodstock story?

My parents Jack and Marion Ayres were back to the land folks who purchased the farm and 525 acres in 1945. My grandparents were from southern Vermont, but my parents were living first in Brooklyn and then in New Jersey but wanting to move to the country. They started making candy and selling local cheese that my father figured out a way to wax in cracker sized bars to sell to my Grandmother’s Christmas card list folks and some local stores. 

I spent my teenage years earning money for my horse’s upkeep by wrapping cheese. In 1962, I married a sugarmaker/dairy farmer, and we started our maple business and sent our milk from our herd of Jersey cows out to local co-op cheese plants to be made into cheese for us. The mail order business grew especially after the internet became popular and after my Mother’s death, we made her living quarters in the 1865 farmhouse into our farm store.  

My two sons, Jeff and Ralph, grew up on the farm, have built homes here and make all the maple syrup from our 10,000 maple trees. We now have two grandchildren in their late 20s that have joined the farm business and hopefully will continue the tradition. I have spent all but the first two years of my life in Woodstock, attended school there, and have been involved with local activities.

What three words sum up Woodstock for you?

Historic, Pretty, Elite

What’s something that Woodstock does better than anywhere else?

Woodstock gives a peaceful setting to help folks relax but still has lots of offers in the way of history, natural beauty, arts, theater, community dinners, and farm-to-table dinners.   

Billings Farm Jersey cows

What tourist attraction lives up to the hype?

A few of the events that live up to the hype are Wassail (in early December), Christmas weekend, Bookstock (think authors and book sales), and Taste of Woodstock. As far as attractions go, I think Marsh Billings Rockefeller National Park and Billings Farm and Museum live up to the history part, as well as Calvin Coolidge Historic Homestead in nearby Plymouth.  In the arts, Woodstock and neighboring towns have Pentangle Arts, Feast and Field dinners and art, Artistree with Grange Theatre, concerts, gallery and all kinds of art classes. For nature, we have Mt. Tom and Mt. Peg with great hiking trails as well as a river walk.

What’s your favorite neighborhood to wander?

Since Woodstock is pretty small, the village comprises two short main streets with very old buildings and tasteful shops. The “Green,” our village park, is the center of the town with lovely old homes, a covered bridge, historic courthouse and library as well as three lovely churches.

Underrated in Woodstock?

Underrated in Woodstock are our gravel (we call the dirt) roads that let visitors see the real Vermont with beautiful, restored farmhouses, great views, and beautiful stone walls. One news story about our farm said, “ Just the ride to the farm is worth the whole trip.”

What’s your Sunday morning in Woodstock?

Since our farm store is open 9-5 seven days a week, my Sunday morning is the same as any other morning– getting our samples ready for the visitors who come to the farm to taste cheese, maple syrup and our various local jams and mustards.

What restaurant do you take friends from out of town for dinner, a casual local’s favorite, and a weekend brunch?

Best dinner would be Prince and Pauper, a casual local spot would-be Mountain Creamery, and weekend breakfast would be Soulfully Good.

Where do you go to get into nature?

I go on my own 550 acres for nature– we have two well laid out walking and hiking trails for our guests but we also have more secluded walking trails for our own family hidden in the maple woods. Mt. Tom which is part of Marsh Billings Rockefeller National Park has many trails which are all free.

South Peak on Mt. Tom

What trends are you noticing in Woodstock right now?

Lots more farm-to-table places to eat. Vermont has more farmers markets per capita than any other state. There are also more young folks moving to Vermont to start small farms and, since COVID, more professionals moving to Vermont to work remotely.

We love sending clients to places that portray an authentic sense of place. How is Sugarbush Farm a reflection of Woodstock?

You can’t come up with a sense of place more than Sugarbush farm. With three generations of family working together, the history of a farm first settled right after the Revolutionary War, working out of an 1865 farmhouse and so much beauty any time of the year.

This interview has been edited for clarity.

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