Find Your TrailExploring and celebrating the place we all love to call home.
VOL. 308 / Find Your Trail
Meet this week’s guest editor, James Moffitt. He is the founder of TrailHead Creative and an avid outdoorsman whose work lives at the intersection of food, the outdoors, sustainability, stewardship, and storytelling. Working with brands ranging from startups to Fortune 200 companies has given him a unique perspective that he brings to every client and project.
James launched TrailHead Creative to merge his passion for storytelling with his love of outdoor adventure. Adding another creative layer to the agency’s Northside headquarters, James also co-founded HomeFire Gallery, an independent art and exhibition space dedicated to creativity and community.
He says the best part about his work is learning from so many different people and walks of life. James is an Eagle Scout, a published author, and a partner in The Fleming Preserve, an upland hunting preserve based in Amelia County, Virginia.
When he’s not working, he’s often spending time with his daughter, tying flies, pursuing wild game, or generally tinkerin’.
This week, James is here to share his tips for exploring and celebrating this place we all love to call home.
Take it away, James ...
Beyond Boundaries R.I.M.B.Y Festival
TrailHead had the honor of partnering with Beyond Boundaries for several years, and their mission resonates closely with our own. R.I.M.B.Y. Festival (Right In My BackYard) is one of their signature annual events. Free and open to the public, it celebrates many of the things that make Richmond special.
RVA RIMBY Festival, hosted on June 7, is a free outdoor festival highlighting the incredible and unique outdoor activities found right here in Richmond’s backyard. The festival features food, drinks, music, games, and prizes, with proceeds supporting outdoor adventure and environmental education opportunities for individuals with disabilities, underserved youth, veterans, and recovery programs.
We’ll be vending at this year’s Fledge Fest. I love that Triple Crossing Beer has doubled down on building community around the outdoors while actively supporting both the Virginia Department of Wildlife Resources and broader conservation efforts.
Triple Crossing is one of those Richmond brands that could easily have gotten “too big” to stay closely connected to the community, but instead, they’ve continued to invest in giving back and supporting the people and organizations around them. Fledge Fest will include a kids’ station with face painting and crafts, falcon cam footage on the big screen, a chance to meet a few feathered friends, exclusive event merch, and a brand-new collaboration beer.
Brent Stubblefield has been a longtime friend, mentor, and partner, and Join or Die Knives is one of those iconic Richmond brands that serves as a steadfast reminder of why I love it here and love working with local businesses.
They offer knifemaking classes year-round — a must-attend experience for just about anyone. It’s hard work, but there’s something deeply rewarding about creating something as timeless as a knife with your own hands. The classes are beginner-friendly, and Brent and his team bring an incredible depth of knowledge and craftsmanship to the experience.
Fun fact: Brent and I actually worked together to make the knife I used to cut my daughter’s umbilical cord. I carry one of his knives every day, and when she’s old enough, my daughter will receive the knife I made for her.
TrailHead was founded in 2020 to combine my passion for the outdoors with my career in content marketing. I wanted to step away from the corporate agency grind and build something rooted in fairness, meaningful work, and the places and communities I care about most.
A big part of TrailHead’s identity comes from wanting to tell outdoor stories differently. So much of the industry focuses on the West, while states like Virginia offer incredible hunting, fishing, mountains, rivers, and coastline right in our backyard. We try to bring that perspective into every campaign and piece of content we create.
Our agency is built around three values: craft, community, and conservation. We believe in creating thoughtful work that lasts, supporting the communities around us, and using our platform to encourage sustainability and stewardship wherever possible.
Most importantly, none of this would exist without the people who have supported us along the way. Thank you to everyone who has supported TrailHead over the years, and especially to Millie Whitmore, Summer Markham, Daisy Norman, and Madeline Guzzo for the work they put in every day.
Built on CareExploring and celebrating the place we all love to call home.
VOL. 307 / Built On Care
Meet this week’s guest editor, Penny Simpson Stein. As co-founder of CARE360, a Virginia-based social venture rooted in Richmond and Charlottesville, Penny is helping empower leaders to navigate a rapidly changing future shaped by AI, sustainability challenges, and social transformation. Through CARELab, CARE360’s educational initiative, she and her team are helping prepare the next generation of leaders, innovators, and changemakers through responsible AI, creativity, and human-centered leadership.
After a career leading innovation and product development teams for a Fortune 100 science and technology company, Penny shifted her focus toward building organizations and initiatives that create meaningful community impact. Her work has ranged from helping revive a woman-owned small business, to building a STEM program for a startup school, to supporting the Science Museum of Virginia and its growing environmental and educational initiatives.
After several career pivots, Penny thought she and her husband were entering an early “second act” focused on family, travel, and leisure. But as the mother of three next-generation children, she found herself drawn toward a bigger question: how do we help prepare young people to thrive — not just professionally, but as thoughtful, ethical, and deeply human leaders in an AI-driven world?
That question gained momentum after Penny met her cofounder, Dr. Ira Kaufman, at a local Encorepreneur event, where they discovered a shared passion for helping the next generation navigate a rapidly changing future. Together, they cofounded CARE360 and CARELab — an effort Penny often describes as a kind of love letter to the next generation and the future they will inherit.
CARELab focuses on helping late high school and college students unlock AI as a strategic thinking partner that expands creativity, innovation, and problem-solving. Students work alongside entrepreneurs, business professionals, and civic leaders to tackle real-world community challenges while strengthening the human leadership skills needed to guide technology wisely and create positive impact.
This July, CARELab will host two immersive summer studios, one at the University of Virginia and the second at the University of Richmond, for students interested in leadership, innovation, responsible AI, and social impact.
We’re excited to have her join us this week to share a few of her favorite Richmond discoveries.
Take it away, Penny…
The Green at the Science Museum of Virginia
If you work or live near the Science Museum of Virginia, I highly recommend taking a lunch break or afternoon walk around The Green. Let’s face it — Scott’s Addition is one of the coolest and fastest-growing parts of Richmond, but it has limited greenspace. In a world increasingly shaped by screens, speed, and constant stimulation, these kinds of community greenspaces are becoming more important than ever.
The Science Museum has already transformed portions of former parking lots into vibrant public greenspace and ultimately plans to convert more than 20 acres of its campus into native landscapes, gathering spaces, outdoor learning environments, and places for exploration and connection. Best of all, it’s free and open to everyone — you don’t even need a museum ticket to enjoy it. I honestly imagine The Green becoming something like Richmond’s own version of Central Park.
One of the things I love most about Richmond is that innovation here often starts at the grassroots level. I’d encourage Richmonders to explore our growing community composting movement through organizations like Compost RVA, which provides residential and business pickup services and community drop-off options across the region. Many people don’t realize how much food waste can be diverted from landfills and transformed into nutrient-rich compost that supports local gardens, farms, parks, and greenspaces.
Did you know that food waste makes up about 24% of material in landfills and is one of the largest sources of methane emissions — a greenhouse gas far more potent than carbon dioxide in the short term? Richmond’s composting movement is a simple but powerful example of circular thinking in action: turning waste into a community resource while strengthening our environmental ecosystem. I love that Richmond is embracing this kind of practical, community-driven innovation!
Vitals: Compost RVA / Residential + Business Composting Services / Community Drop-Off Options
Experiences That Prepare Students for an AI-Driven Future
One of the best investments we can make as a community is helping young people prepare for a world being rapidly reshaped by AI and technological change. We’re entering what I often think of as the AI-Humanity Paradox: as technology becomes more powerful, uniquely human capabilities like empathy, ethics, creativity, collaboration, and critical thinking become even more important.
That’s why I’m passionate about programs like CARELab, which help students strengthen leadership, adaptability, innovation, and purpose-driven thinking alongside technological fluency. This summer’s CARELabs at the University of Richmond and University of Virginia will bring together students, entrepreneurs, business professionals, and civic leaders to tackle real-world community challenges while exploring responsible AI and human-centered leadership.
CARELab partners with the University of Virginia Contemplative Sciences Center and the University of Richmond Innovation Studio to provide immersive, intergenerational learning experiences for late high school and college students. Through the program, students work alongside entrepreneurs, business professionals, and civic leaders while developing leadership, collaboration, strategic creativity, and responsible AI skills. Students also tackle real-world community challenges provided personally by city mayors.
CARELab studios combine human-centered leadership and mindfulness, entrepreneurship and innovation, responsible AI and prompt engineering, sustainability and social impact, design thinking, and team collaboration and public speaking. Students leave with stronger confidence, expanded leadership capability, and a deeper understanding of how to use AI and innovation to create positive impact in both career and community. Limited partial and fully sponsored seats are available!
Something Worth Barking AboutExploring and celebrating the place we all love to call home.
VOL. 306 / Something Worth Barking About
Meet this week’s guest editor, Tamsen Kingry. Tamsen is the CEO of the Richmond SPCA, a nonprofit, no-kill humane society that saves the lives of 4,000 homeless animals each year. The organization also delivers a wide range of safety-net programs — including a pet pantry, behavior helpline, high-volume spay and neuter services, crisis boarding, low-cost and full-service veterinary care, youth education, and training — reaching tens of thousands of pets and the people who love them across the region.
If you had told Tamsen during her senior year at VCU that her internship would turn into a 24-year career, she might have asked what you were feeding the animals. But that’s exactly what happened. In 2002, thanks to some serendipitous timing (and a departing communications manager), she stepped into her first full-time role at the Richmond SPCA.
Over the last two decades, she has had a front-row seat to the organization’s evolution and growth, working in communications, development, and operations before becoming CEO in 2019. Along the way, she has adopted three dogs and two cats, fostered many others, and happily played matchmaker for countless friends looking for a new companion. Outside Richmond, she serves on Best Friends Animal Society’s Network Strategy Council, collaborating with shelter and rescue leaders across the country to strengthen the future of animal welfare.
Tamsen has called Richmond home since 1999 and shares her home with her husband, daughter, and adopted dog and cat. When she’s not at the humane center, you can find Tamsen — often joined by her dog Bart — at some of her favorite spots in the Fan, including Jardin, Susie’s, Celladora, and Blanchard’s. She’s also a frequent flier at the Broad Street Lowe’s, where she never misses the chance to say hello to the one-and-only Francine.
Take it away, Tamsen …
Bark in the Park
Bart isn’t the only one in my family angling for a game of fetch. When we’re not at my daughter’s softball games, we enjoy cheering on our local baseball team, the Richmond Flying Squirrels. I was fortunate to get a sneak peek of CarMax Park (a neighbor of the Richmond SPCA) before it opened and cannot wait to catch up with Nutsy and Nutasha at the first dog-friendly game the team hosts this season.
The Flying Squirrels return home against the Binghamton Rumble Ponies on Tuesday, May 19. Bark in the Park takes place every Wednesday home game from now through September 9, so grab your furry friend and head to the ballpark. During Bark in the Park games, presented by Tito’s Handmade Vodka, a portion of proceeds from the Squirrel Chaser specialty cocktail will be donated to the Richmond SPCA.
Vitals: Binghamton Rumble Ponies, Tuesday, May 19 / Bark in the Park, every Wednesday home game through September 9 / CarMax Park, 1771 Encore Avenue
Sharp's Island
Now I’m letting you in on a well-kept secret. There’s a private island full of fascinating history near the Mayo Bridge called Sharp’s Island. The only way to access it is by kayak or canoe, which is part of the charm and adventure — and very Richmond. It’s an excellent place to access the James River and camp, offering the only legal camping within Richmond city limits.
Hollywood Cemetery is a great place to walk while taking in breathtaking views of downtown Richmond and the James River. Not many cities give you high-rises, train crossings, bridges, and rapids all in a single glance. It’s one of the things that makes Richmond unique, and I like to take advantage of that whenever possible.
I also recommend joining a History Hounds tour, a partnership between the Richmond SPCA and The Valentine Museum. You can explore the history of some of Richmond’s most iconic neighborhoods, including Church Hill and the Museum District, with your dog at your side. You’ll even get to meet a dog available for adoption.
Want to take your exploration of Richmond to the next level? Join the Richmond SPCA for our Amazing Tails Scavenger Hunt on Saturday, May 30.
Think you have what it takes to race, solve, and strategize like a pro? Inspired by The Amazing Race, this interactive scavenger hunt is your chance to compete for a cause. Gather a team and hit the streets of Carytown, tackling clues and connecting with local businesses along the way. Every step supports the lifesaving work of the Richmond SPCA — and your team could take home a prize.
Registration closes on May 20, and only 20 teams can compete, so secure your spot now. Keep tabs on all upcoming events, classes, and more at the Richmond SPCA!
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