Hike & Explore Jack London State Historic Park

Jack London’s 1,400-acre ranch is open every day of June and absolutely stunning this time of year. Explore over 20 miles of trails — from easy meadow walks to the forested ridge above Beauty Ranch — and visit the Wolf House ruins, the House of Happy Walls museum, Jack London’s Cottage, and the Pig Palace. Second-growth redwoods, blooming wildflowers, and sweeping Sonoma Mountain views make this one of the best state parks in California.

Free docent-led tours of the Wolf House & Grave Site and Beauty Ranch run on weekends. No dogs on trails.

Benziger Family Winery Tours & Tastings

One of the most celebrated biodynamic wineries in the country, Benziger offers daily tastings and their signature open-air tractor tour through the estate vineyards. The June tasting lineup features their estate Sonoma Mountain Cabernet Sauvignon and summer rosés at their best. Walk-ins are welcome in the tasting room; the tractor tour and specialty tastings should be booked in advance. Leashed dogs welcome in the tasting room.

Quarryhill Botanical Garden

Nestled in the Mayacamas Mountain foothills, Quarryhill is one of North America’s premier collections of wild-origin Asian plants — 25 acres of rare maples, magnolias, peonies, and woodland plants most people have never seen. June brings summer color to the garden’s winding gravel paths, reflecting ponds, and seasonal waterfalls. Docent-led tours are available; self-guided walks are easy and relaxing. A true hidden gem in the Sonoma Valley.

Sonoma Tuesday Night Farmers Market

The weekly Sonoma Tuesday Night Market is one of the liveliest events in the valley and just a short drive from Glen Ellen. Local farms bring peak-season strawberries, stone fruit, greens, and artisan products, while food vendors, live music, and the energy of a long summer evening make this a can’t-miss tradition. Perfect for grabbing dinner ingredients or just soaking up the Sonoma Plaza vibe after a day of hiking or wine tasting.

“Spirit Guides: Fantastical Creatures” — Sonoma Botanical Garden

Running throughout the spring and summer season, this outdoor art exhibition features large-scale sculptural works by Oaxacan folk artists Jacobo and María Ángeles, whose fantastical carved and painted creatures are displayed throughout the garden’s landscape. The pieces range from mythological animals to imaginative spirit beings, and they weave beautifully through the botanical collections. A memorable experience for adults and children alike.

Country Summer Music Festival

Northern California’s biggest country music festival returns to the Sonoma County Fairgrounds for three days of sun, dancing, and live music. The 2026 lineup features Grammy winner and three-time Entertainer of the Year Keith Urban headlining Saturday, June 13, alongside Cole Swindell, Koe Wetzel, and 20+ additional artists across the Chevrolet Main Stage and Redwood Credit Union Community Stage. On-site camping, local food vendors, and a VIP Country Club experience are all available.

An easy 30-minute drive from Glen Ellen — make it a full Wine Country weekend.

Broadway Under the Stars: Ain’t Too Proud

Transcendence Theatre Company’s 15th season of Broadway Under the Stars opens with the Tony Award–winning musical Ain’t Too Proud: The Life and Times of The Temptations. Following the legendary Motown group from the streets of Detroit to the Rock & Roll Hall of Fame, this electrifying show features 42 Top Ten hits, signature choreography, and an emotionally powerful story of brotherhood and sacrifice.

Arrive at 5pm for a Sonoma-style pre-show picnic with local food, wine, and live music on the Field of Dreams lawn. Shows run at 7pm. A special Juneteenth celebration performance is scheduled for Friday, June 19, with ASL interpreters available.

Community Day at Jack London State Historic Park

Jack London State Historic Park hosts a special community day in partnership with the Sonoma Community Center. This all-ages event invites families and locals to connect with the park through guided activities, nature programming, and ranger-led exploration. It’s a wonderful opportunity to experience this historic property with community spirit — and one of the best Saturday outings of the entire summer in Glen Ellen.

NASCAR Cup Series at Sonoma Raceway

High-speed NASCAR action returns to wine country at the iconic Sonoma Raceway road course — one of only two road courses on the Cup Series calendar. The twisting 1.99-mile circuit through the Sonoma Valley hills makes for one of the most visually spectacular races of the year. Combine it with a Glen Ellen winery visit for a true wine country race weekend. Book accommodations in the area well in advance as this event draws large crowds from across California.

The Glen Ellen Green Tour: Park + Garden + Winery

This guided half-day tour is Glen Ellen’s best all-in-one experience. Starting with a docent-led walk through Quarryhill Botanical Garden’s 25 acres of rare Asian plants, the tour continues into Jack London State Historic Park for history and trails, and wraps with a picnic lunch and wine tasting at Benziger Family Winery. A $59 all-inclusive experience you can’t recreate on your own. Advance reservations are required — book at least two weeks before your visit.

Sonoma Valley Regional Park Trail

Sonoma Valley Regional Park’s Sonoma Ridge Trail climbs from the valley floor up to sweeping views across the Valley of the Moon — all the way to San Francisco Bay on a clear June morning. The park is less crowded than Jack London State Historic Park, free to visit, and allows dogs on leash. Multiple trailheads and loop options make it accessible for all fitness levels. June wildgrass and oak woodland views are stunning.

Talisman Wines Tasting Room

Located right in the heart of Jack London Village, Talisman is a small-production Pinot Noir specialist sourcing from single-vineyard sites throughout Sonoma County. Their focused lineup of cool-climate Pinots is exceptional and the intimate tasting experience is the opposite of a big commercial operation. Walk-in friendly on weekends. Pair with a stroll through the Village’s galleries and the Songbird Parlour next door for a perfect Glen Ellen afternoon.

B.R. Cohn Winery & Olive Oil Farm

Founded by rock music legend Bruce Cohn — longtime manager of the Doobie Brothers — B.R. Cohn is a beloved Glen Ellen institution. Their estate on Sonoma Mountain produces excellent Cabernet Sauvignon and Merlot from ancient olive tree-lined vineyards, plus an acclaimed line of estate-grown olive oils. The outdoor patio is one of the most beautiful tasting spots in the valley. The winery hosts periodic summer concerts on the property — check their calendar for June dates.

Imagery Estate Winery & Art Gallery

Imagery is one of the most unusual wineries in Sonoma — every bottle features original art commissioned from emerging artists, and their tasting room doubles as a gallery with an ever-rotating collection. The winery produces a fascinating range of varietal bottlings from around Sonoma County including rare varieties you won’t find elsewhere. The art experience alone makes it worth a visit, and the wines consistently over-deliver. A cultural stop as much as a wine stop.

Jack London Village & Songbird Parlour

The historic Jack London Village complex on Arnold Drive is Glen Ellen’s social hub — a cluster of artisan shops, wine tasting rooms, and the beloved Songbird Parlour restaurant. June evenings on the Village patio are among the most pleasant in Sonoma Valley. Songbird features rotating local performers and a menu built around Wine Country seasonal ingredients. Stroll, taste, and linger — this is what small-town Sonoma Valley is all about.

Sugarloaf Ridge State Park Hiking & Stargazing

Just 15 minutes from Glen Ellen, Sugarloaf Ridge State Park offers some of the most dramatic hiking in Sonoma Valley — including the summit of Bald Mountain at 2,729 feet with panoramic views from the Sierra Nevada to the Pacific. In June, the park also hosts its weekly yoga hikes and trail crew Saturdays. The Robert Ferguson Observatory on-site runs public stargazing nights on weekends — June’s clear skies make these events exceptional.