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The Maine Playweek · Jul 21, 2026

Romanticism and Rock Climbing: a review of documentary Catching Pinecones

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The Maine Playweek, Scott Whiting · The Maine Playweek

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I’ve always been a sucker for capital-R Romantics. For the uninitiated, Romanticism isn’t about passionate bodice-ripping (necessarily), but an arts movement grounded in the love and reverence of nature and the embrace of individualism. If I had to sum up Romanticism in one picture, Casper David Friedrich’s painting Wanderer Above the Sea of Fog would have to be it (and Wikipedia seems to agree). And if I had to sum up Romanticism in a moving picture, as a documentary making Romantic art reality, then Catching Pinecones is hard to beat.

Prior to watching, I had never heard of Herb and Jan Conn. Apparently, in the world of rock climbing and spelunking, they’re kind of a big deal. Many records and notable firsts in climbing and cave exploration belong to them, which the film details lovingly and I shan’t recap here. But the Conns are so much more than a pastime they seemed to have picked up by accident.

Beginning with a humble courtship in the 1930’s, Jan and Herb cultivated a partnership and lifestyle that those of us living now in 21st-century America can only dream of. They buy hundreds of acres of property in the Black Hills of South Dakota with the ambition of climbing every nubbly, rocky precipice within. A hollow in the same property is furnished with rubblestone and timber to become their full-time, off-the-grid residence (punningly known as “The Conn Cave”). Herb uses his engineering degree to calculate that nearby Jewel Cave, once thought to be a “small” cave, is actually thousands of miles deep, with only hundreds thus far explored by humans (namely, themselves). And Jan nurtures her talents as a lyricist and multi-modal musician: indeed, the film’s soundtrack is entirely her own works.

It’s hard to not love the Conns as the movie documents the pictures, diaries, and other ephemera that survive them. Jan Conn, who passed away in 2023, sits with us on and off screen for much of the feature, telling us tales throughout the years that would seem too fantastic to be real were there not proof otherwise. But it’s the footage of the lone wanderers, standing atop one of the many Needles, gazing afar, that really makes my Romantic heart race. Casper David Friedrich dreamt it; the Conns actually did it.

Catching Pinecones is playing on Friday, July 24 at 5pm at the Portland Museum of Art, as part of the Maine Outdoor Film Festival.

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