When people ask me where I’m from, without pause, I tell them Chicago. After all, I cut my teeth in the Second City and continue to possess a lasting reverence for her architecture, culture, food and sports. Then, in my next sentence, I mention that I also lived in San Francisco for several years (4th-8th grade & one year after college) and I came to love the idiosyncratic sloping beauty of her streets and the iconoclastic ethos of her people. (Sidenote: All cities I love are female thanks to RHCP’s Under the Bridge). However, when considering the lasting impact of these two places on me, I can only come to one conclusion: Charlottesville is where I belong. While Chicago (15 years) and San Francisco (7 years) housed my formative years, Charlottesville (20 years) is where I truly became the man I am today.
Because of this revelation, I decided it was high time to walk the 20-mile Rivanna Trail to experience the beauty of Charlottesville in a whole new way. The Rivanna Trail began as an audacious vision in the 1990s to create a trail that would encircle Charlottesville and thread her diverse landscapes together in the process. Picture a ribbon of green winding through urban spaces, lush forests, and serene riverbanks, offering a respite from the hustle and bustle of daily life.

The Rivanna Trail started with a group of passionate locals who, in 1992, formed the Rivanna Trails Foundation (RTF). Their mission required the cooperation of landowners, the city, and countless volunteers. Starting from Riverview Park, it meanders through neighborhoods, wooded hills, and alongside the Rivanna River. One can witness the shifting landscapes – from the manicured lawns of city parks to the wild, untamed beauty of the river’s edge. It’s a microcosm of Charlottesville’s natural diversity.
Along the trail, the legacy of the land is palpable. You might stumble upon remnants of old mills that once harnessed the river’s power or cross paths with historic railway lines that speak of an era when rail was king. Each step on the Rivanna Trail is a step through history, intertwined with the natural splendor of Virginia’s Piedmont.
Walking the Rivanna Trail is an experience of connection – to nature, to history and to the community. It’s a reminder of what can be achieved when people come together with a shared vision, creating something enduring and enriching for future generations.
Recommendations:
- One change of underwear and shirt (if hiking in summer). You will soak through them both during 20-mile journey. When you pop into civilization to use a public restroom, I’d recommend some fresh duds, it’s really crucial.
- Bring a mobile charger. Nothing worse than losing your phone capabilities halfway through an 8-hour hike.
- Notebook and Pen. During your hike you will have ideas, inspiration and reflection. When you stop to rest, take a moment to record these for future investigation.
- Water Shoes or Water Friendly Sandals (Keens/Tevas). There are 5-10 water crossing spots during this hike with stepping stones. You should be OK but if it has rained a lot recently the water might be high enough to get your feet wet.
- Gold Bond powder (if hiking in summer). For the boys, generally and figuratively.
- Frozen Grapes. Because, really, why wouldn’t you?
Non-Negotiables (h/t to Carmy)
- Safety Concerns. This is an urban walking trail and unfortunately assaults do happen occasionally. I would recommend hiking in pairs or, if solo, having a weapon handy (I took bear spray). Also, bikes will approach behind you going very fast at times, a good rule of thumb is the “one earbud policy” to ensure you remain aware to your surroundings.
- AllTrails App. While trail maps and descriptions are posted online, there are times when the trail isn’t marked well. Using this app cuts through the guesswork so you always know exactly where you are. There is also a “live share location” feature so you can let a friend know where you are in case something goes wrong. It’s $35/year for the service but worth it, especially if you plan to hike other local trails.

On Saturday, June 29th I awoke at 5:30am, stretched and set off into the hazy pre-dawn morning.
NEXT: The Charlottesville Loop (Rivanna Trail): Trail Twilight




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