Weekend Trips From Healdsburg CA

Located in Sonoma County’s wine country, Healdsburg offers a prime jumping-off point for discovering other parts of Northern California. While Healdsburg has its own charm and top-tier wineries, spending a couple of days exploring nearby destinations offers a change of pace and new experiences. These weekend trips from Healdsburg combine local flavor, scenic surroundings, and accessible drives.

Here are eight carefully selected weekend destinations that offer something distinct.

Santa Rosa, only 20 minutes from Healdsburg, often gets overlooked, but it offers a lot for a quick weekend reset. Explore downtown’s Railroad Square, where you’ll find antique stores, wine bars, and shops like Ooh La Luxe. The area also features coffee shops and tasting rooms within walking distance.

Don’t miss the Luther Burbank Home & Gardens or the Charles M. Schulz Museum, both located within city limits. For shopping, stop at Montgomery Village, an open-air shopping center. With wine, food, and entertainment in one place, Santa Rosa works well for spontaneous weekend trips from Healdsburg.

Guerneville is only about 30 minutes away, but it feels like a true escape, surrounded by redwoods and centered along the Russian River. This town has long attracted artists and creative types, which is reflected in its small businesses and relaxed pace. Nature lovers can head to Armstrong Redwoods State Natural Reserve to walk among giant trees. Lodging options range from rustic cabins to boutique inns like The Stavrand, which blends modern comfort with historic architecture.

Calistoga lies about 45 minutes from Healdsburg and has a slower pace than nearby Napa. Known for its geothermal features, many visit for spa treatments and mineral pools. The Calistoga Spa Hot Springs and Indian Springs Resort are popular places to book mud baths and soaking sessions.

Calistoga’s walkable downtown includes shops like Blackbird of Calistoga for lifestyle goods and curated clothing. For food, Sam’s Social Club offers American cuisine in a modern setting. Tasting rooms like Tank Garage Winery provide a different take on wine, with themed labels and unconventional blends. Many planning weekend trips from Healdsburg appreciate the contrast between Calistoga's laid-back charm and other wine towns' formality.

Napa Valley is just over an hour from Healdsburg and offers a deep contrast in atmosphere. You’ll find a more polished wine-tasting scene with grand estates like Castello di Amorosa and Domaine Carneros, known for sparkling wines and estate views. Tastings often require reservations, and some experiences last several hours.

Downtown Napa provides walkable access to upscale shops and restaurants. Browse First Street Napa or the Oxbow Public Market to sample artisan foods. Dining ranges from fine-dining spots like La Toque, which is popular with both locals and visitors.

Point Reyes Station is about two hours away by car and offers a quiet retreat with coastal trails and a small-town main street. It's ideal for hiking, browsing local shops, and tasting fresh local food. Begin with a visit to Point Reyes Books, an independent bookstore with community events and literary titles. Nearby, Toby’s Feed Barn offers everything from organic groceries to handmade ceramics.

The food scene emphasizes seasonal, local ingredients. Station House Cafe serves hearty brunches and seafood. For baked goods, Bovine Bakery is a staple. Outside of town, drive to Point Reyes Lighthouse or hike the Tomales Point Trail, which offers elk sightings and dramatic views. It’s a peaceful destination for weekend trips from Healdsburg.

Mill Valley is tucked into the foothills of Mount Tamalpais and takes about 90 minutes to reach. The downtown area features upscale boutiques like The Store and Ambatalia, which focuses on sustainable textiles. Then head to the Mill Valley Lumber Yard, which now houses shops and restaurants.

Outdoor lovers can hike to Cascade Falls or visit nearby Muir Woods National Monument. For dining, Bungalow 44 serves wood-fired dishes in a lively setting, while Tam Junction has local pop-ups and cafés. Mill Valley’s natural beauty and high-end retail offer a relaxing and engaging weekend escape.

Just north of San Francisco and around 90 minutes from Healdsburg, Sausalito offers waterfront dining and upscale shopping with stunning views of the Bay. If the weather’s nice (it usually is), walk along the boardwalk or browse art galleries.

Dining options include Barrel House Tavern with patio views and Le Garage, a French bistro tucked into a former auto shop. You can also take a short kayak ride or explore the Bay Model Visitor Center, which houses a scale model of the San Francisco Bay. It’s a good stop for those seeking quick weekend trips from Healdsburg with waterfront scenery.

Mendocino is about a two-and-a-half-hour drive from Healdsburg, and it feels like a full escape. The town rests on cliffs above the Pacific Ocean, offering panoramic views and coastal trails. It’s known for its art galleries and local artist studios. You can visit Highlight Gallery or Mendocino Art Center for local exhibits.

For lodging, many choose historic inns like the Blue Door Inns or oceanfront options with fireplaces and views. Don’t miss Mendocino Jams & Preserves, a small shop specializing in local handmade goods. While you're in the area, take a walk through Russian Gulch State Park or enjoy a meal at Cafe Beaujolais, which is housed in a Victorian farmhouse.

If you're considering buying or selling property in Healdsburg or the surrounding wine country, connect with a trusted local expert who understands the fast-paced Bay Area market and the peaceful charm of Sonoma and Napa Counties. Ceci Cook brings over a decade of real estate experience, guiding clients through transactions across the Peninsula, South Bay, and North Bay.

If you're planning to make your next move in Healdsburg, reach out to Ceci Cook for reliable guidance and a personalized approach to real estate.