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!
Richmond, Go Wild 🐾Exploring and celebrating the place we all love to call home.
VOL. 304 / Go Wild
Meet this week’s guest editor, Krista Weatherford, Maymont’s Director of Programming and Curator of Natural Resources. Krista exudes a lifelong passion for wildlife and natural resources and shares it enthusiastically with everyone she meets. As a leader of both education programs and animal care at Maymont, she infuses everything she does with a sense of fun and a deep respect for people and animals.
In addition to planning educational programs for more than 18,000 students who visit Maymont each year, as well as summer camps, night hikes, citizen science programs, and more, Krista supervises a dedicated team of animal care specialists who care for more than 300 animals at Maymont — from tiny seahorses to North America’s largest land animal, the bison.
Even when she’s not at Maymont, Krista is an advocate for the environment as a facilitator in Project WET, Project WILD, and Project Learning Tree. She is a Virginia Master Naturalist with the Pocahontas Chapter and a Certified Interpretive Guide. Her hobbies also reflect her love of the natural world, as she enjoys kayaking, hiking, and observing wildlife.
Krista has been with Maymont for 11 years and in the field of environmental education for a total of 25 years, including teaching and managing several programs in Virginia State Parks and at Georgia Southern University’s Center for Wildlife Education. She took time out of her busy schedule this week to offer her tips for exploring and celebrating this place we all love to call home.
Take it away, Krista ...
Virginia Wildlife Trail Grrrrand Reopening at Maymont
After two years of major enhancements, celebrate the reopening of Maymont’s beloved Virginia Wildlife Trail, a forever home for rescued and rehabilitated native wildlife nestled in the heart of Richmond. On May 2, from 10 am to 4 pm, enjoy free entertainment, games, and activities while you explore the new and remodeled habitats, with more accessible pathways, new interpretive signs, and more ways to view our wildlife residents — including old friends Big Bear and Little Bear, and our newest residents: two porcupines and a coyote!
Learn about the importance of pollinators in the environment, planting native plants, and how to care for beehives, presented by the Rockwood Park Backyard Beekeepers Association and the Bumblebee Jamboree at the Chesterfield County Fairgrounds. From 10 am to 3 pm, enjoy live music by the Bee Flats, plus children’s activities, local honey and beekeeping supplies for sale, bee-friendly plants, educational talks, face painting, food trucks, and more.
Vitals: 15th annual Chesterfield Bee Festival / Saturday, May 2, 10:00 a.m. - 3:00 p.m. / Free, children welcome / Chesterfield County Fair Grounds, 10300 Courthouse Road
Clean the Bay Day at Pocohontas State Park
Each year, Virginia State Parks participates in the Chesapeake Bay Foundation’s Clean the Bay Day, an event dedicated to protecting and preserving the Chesapeake Bay watershed. Park visitors are invited to join a clean-up to help remove litter, debris, and pollution from rivers, streams, and shorelines that feed into the Bay, contributing to the health of the Bay’s ecosystem and ensuring cleaner water and safer habitats for wildlife. Volunteers will work alongside park staff to keep our natural areas beautiful for everyone to enjoy. This event is a great opportunity for individuals, families, scout groups, and community organizations to give back while spending time outdoors. Wear sturdy, closed-toe shoes and dress for the weather. Bring water, sunscreen, and work gloves; trash bags and additional supplies will be provided.
Vitals: Clean the Bay Day / Saturday, May 2, 9:00 a.m. - 12:00 p.m. / Free, children welcome / Advance reservations required / Pocahontas State Park, CCC Field, 10301 State Park Rd., Chesterfield
More from Krista.
The newly enhanced Virginia Wildlife Trail is included in Maymont’s free general admission, open from 10 am to 7 pm during daylight saving time and from 10 am to 5 pm when days are shorter. Additional guided experiences and up-close programs with some of Maymont’s wildlife are available for advance reservation at Maymont.org/tours. All program fees help support the operations of the nonprofit Maymont Foundation, which cares for the historic collections, gardens, and animals, and provides educational programs.
Don’t miss the visiting wildlife that stop in at Maymont as part of the James River wildlife corridor. Wildlife photographer Bill Draper frequently documents some of the deer, foxes, groundhogs, birds, and butterflies that use Maymont as a temporary or permanent home.
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