The 2026 Wilbraham Hill Climb with the 1929 Duesenberg Model J-268 Convertible Coupe

Monson Road, Wilbraham, Massachusetts • May 9, 2026

By Nicole LeBoeuf
The 1929 Duesenberg Model J-268 Convertible Coupe glistening in the rain at the 2026 Wilbraham Hill Climb in Wilbraham, Massachusetts.
The 1929 Duesenberg Model J-268 Convertible Coupe glistening in the rain at the 2026 Wilbraham Hill Climb. Photograph by Josh Sweeney of Shoot for Details.

Huge thank you to Josh Sweeney of Shoot for Details for capturing these moments last weekend at the Wilbraham Hill Climb. Despite the rain, we were happy to be a part of this historic event, testing antique automobiles and motorcycles against a steep, mile-long stretch of Monson Road in Wilbraham, Massachusetts. Despite this event first being hosted in 1908, it was the first time the 1929 Duesenberg Model J-268 Convertible Coupe attempted it, and we were not deterred by a little rain. Turns out, she glistens even more, so stay tuned for video of our adventure!

(And thanks for joining us AA Indian!)

Dick Shappy behind the wheel of the 1929 Duesenberg Model J-268 Convertible Coupe at the 2026 Wilbraham Hill Climb.
Dick Shappy behind the wheel of the 1929 Duesenberg Model J-268 Convertible Coupe in the rain.
The 1929 Duesenberg Model J-268 Convertible Coupe on rain-slicked Monson Road at the 2026 Wilbraham Hill Climb.
Heading down rain-slicked Monson Road in Wilbraham, Massachusetts.

The 1929 Duesenberg Model J-268 Convertible Coupe went to the Wilbraham Hill Climb last week. Check out the video debuting tomorrow or visit the Dick Shappy YouTube channel and subscribe if you haven't already!

1929 Duesenberg Model J-268 Convertible Coupe in Wilbraham, Massachusetts.
1929 Duesenberg Model J-268 Convertible Coupe in Wilbraham, MA.
Side-mounted spare tire and chrome wire wheel on the 1929 Duesenberg Model J-268 Convertible Coupe at the 2026 Wilbraham Hill Climb.
Side-mounted spare tire and chrome wire wheel on the 1929 Duesenberg Model J-268.

2026 Wilbraham Hill Climb Photo Gallery

Click any photo to view full size.

Raindrops on the chrome Duesenbird hood ornament of the 1929 Duesenberg Model J-268 Convertible Coupe
Dick Shappy in the 1929 Duesenberg Model J-268 Convertible Coupe at the 2026 Wilbraham Hill Climb
Visiting with Dick Shappy beside the 1929 Duesenberg Model J-268 Convertible Coupe at the 2026 Wilbraham Hill Climb
Dick Shappy at the wheel of the 1929 Duesenberg Model J-268 Convertible Coupe in the rain at the 2026 Wilbraham Hill Climb
1929 Duesenberg Model J-268 Convertible Coupe at the 2026 Wilbraham Hill Climb
Nicole LeBoeuf with the 1929 Duesenberg Model J-268 Convertible Coupe at the 2026 Wilbraham Hill Climb
1929 Duesenberg Model J-268 Convertible Coupe on display at the 2026 Wilbraham Hill Climb
Nicole LeBoeuf beside the 1929 Duesenberg Model J-268 Convertible Coupe at the 2026 Wilbraham Hill Climb

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