Chimbarazo Park Trail is a 0.9 mile moderately trafficked loop trail located near Richmond, VA that features beautiful wild flowers and is rated as moderate. The trail offers a number of activity options and is accessible year-round.
I live near this park so this is a route I walk with my dog frequently. It's rated as moderate difficulty, but if you park up near Broad instead of down the hill, it's quite easy. There is an off leash dog park at the bottom of the hill. It's a great spot to watch sunrises and sunsets, and there is a battlefield museum located in the middle of the park if you want to stop inside (not sure of their hours).