This is a great little wine country hike that begins very near the Simi Winery in Healdsburg. Plan on spending about an hour to an hour and a half enjoying the beauty and solitude of the open space wilderness area just above a residential housing development in northern Healdsburg. It is best to take this hike before lunch when cooler temperatures prevail. The loop trail described, the one we hiked, is about 2 miles in distance and mostly a moderate effort. It is a popular trail with dog walkers and joggers from the local community.
Start at the trailhead marked “The-all-Oaks-Trail.” This is a beautiful stretch lined with oaks, Madrone, and Manzanita. Watch 
out for poison oak. After about a half mile, you will see a sign pointing to the Ridge Trail straight ahead and to the Russian River Overlook to the right. Take this spur to the right and up to the overlook, just a few minutes walking distance away. What a view! This overlook provides a view of the Alexander Valley and vineyards, the Mayacamus Mountains, and the Russian River. Get back to the trail and continue on the Ridge Trail. There are three additional overlooks on the Ridge Trail: Mayacamus Overlook, Coyote Hill Overlook, and Nancy’s Hill. These are all nice views but nothing beats the Russian River Overlook. Continue on the Ridge Trail to the pond and you have completed the loop.
How to get to the Healdsburg Ridge Trail
From the Healdsburg Plaza in the downtown area, drive north along Healdsburg Avenue for 2 miles and turn right on Parkland Farm Blvd. It is just before the Simi Winery. Take this road to about 3/4 of a mile on Bridle Path Way and turn right onto Arabian Way. Park and hike.
After the hike
Now it is time to wine taste and picnic. The closest winery and one of the oldest in California is the Simi Winery. Simi is celebrating 140 years of making wine. Simi is one of the first wineries we visited many moons ago when we began our wine country travels. There are two excellent wine routes close to the Healdsburg Ridge hike. The Alexander Valley Wine Route includes Simi Winery and some really fun wineries along the beautiful backroad of Highway 128. The Geyserville Wine Route takes you north to Geyserville. Have you been to the Francis Ford Coppola Winery? It is a great experience for both adults and kids. Read more about Coppola. The town of Healdsburg ranks as one of the best wine towns anywhere in the world. In one small area there are not just restaurants and lodging but boutique shopping, art galleries, and wine tasting bars.
More on hiking and running in Sonoma wine country
- Armstrong Grove hiking – Russian River Valley and Redwood trees
- Riverfront Regional Park – Eastside Road wineries
- Hiking in other wine regions of California wine country
- When to visit Sonoma wine country