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Old Time Fair at the Woodstock History Center

From The Blog Weekend Fun: Race to adventures like the Woodstock Triple Crown, Old Time Fair, Painting on the Rocks, & more

Just like that, summer falls into September

Are you ready for the mid-month fun awaiting this Thursday through Sunday?

Horseback Riding
Sip n Paint Masterpieces
Billings Farm & Museum

Then, starting at 6 PM, choose from two types of fun:

Fall Golf at the Woodstock Inn's Country Club
Jim Westphalen

5:30 - 7 PM: Ladies, looking for something different? Get ready for some heart-pumping fun during women’s evening mountain biking rides at Suicide Six Bike Park.


9 AM – 12 PM: Lace up for a race that’s equal parts exhilarating and welcoming during this week’s Parkrun – a global timed 5k at Marsh-Billings-Rockefeller NHP. Walk, run, and soak up the early fall sun! Register online now.

Early birds get the worm beginning at 9:30 AM, with a cornucopia of activities to choose from:

1 – 4 PM: For just a quarter, step right up for an Old Time Fair right in the heart of Woodstock village! Live music, crafts, games, treats, and a photo booth with historic clothing await on the back lawn of the Woodstock History Center.

Old Time Fair at the Woodstock History Center
Woodstock History Center
Old Time Fair at the Woodstock History Center in Woodstock, VT

Reserve your spot at one of two tours to satisfy your history and wanderlust:

6 – 8 PM: Later listen as award-winning art historian, critic, author and podcaster Tyler Green explores a groundbreaking 19th century photographer with the presentation, Carleton Watkins: Making the West American. Green’s talk explores the surprising relationships between Carleton Watkins, New England, and the national park idea – including connections to Frederick Billings and Woodstock, VT. This event is free at Billings Farm & Museum, but reservations are recommended.


9 AM: The Naked Table Community Project is back, 11 years strong with the Annual Community Table Making Event on the Green in Woodstock! Follow up the action with a forest walk through the national park at 12 PM then lunch on the tables lined up on the Middle-Covered bridge at 2 PM. Served “family” style. There will be a memorial tree planting ceremony on the green at 3pm for Phil Swanson, Woodstock Town Manager for 34 years. There will be live music throughout the event. Organized by Charles Shackleton. See link for reservations and details.
Annual Naked Table lunch on the Middle Covered Bridge

5 – 8 PM: When gardeners and chefs collaborate, we all win! Sample fresh-as-they-get flavors like Vermont Goat Cheese Toast, Tomato and Olive Tarts, Braised Local Lamb Shank, and more – all at the Red Barn Dinner Fall Foliage Series at Kelly Way Gardens. See link for pricing and reservation details.