Sonoma Wine Country overnight 🍷🚲🚂
What:
An overnight wine tour of Sonoma County.
Caltrain to ferry to SMART train, winery-hopping in Windsor, and a 46-mile ride home over the Golden Gate the next morning.
Dates: Saturday–Sunday, June 27–28, 2026
Who: Adults, 21+ — bicycles required
Overnight: Windsor (hotel TBD — buddy up on rooms to keep it reasonable)
Saturday
Getting There
We’ll meet at the 4th & King Caltrain station in San Francisco. Bring your bike — Caltrain allows bikes on board with no reservation needed.
From San Francisco we’ll catch the Golden Gate Ferry to Larkspur, which also accommodates bicycles. Then we board the SMART train northbound, riding all the way to the Windsor station — the current northern terminus, which opened in May 2025.
Windsor Tasting Rooms
Windsor’s SMART station drops steps from the Town Green, a pedestrian plaza surrounded by tasting rooms.
We’ll hit as many as daylight and stomachs allow:
- Bellacana Vineyards — the only tribally-owned winery in North America, right on the Town Green. Sparkling, Sauv Blanc, Cabs. Opens 11:30am.
- Mutt Lynch Winery — “Bark Less. Wag More.” Dog-friendly, limited-production wines, great outdoor seating. A crowd favorite.
- Baldassari Wine Lounge — cozy lounge with a 6-wine flight (RRV Pinot Noir, Chardonnay, Malbec, Syrah, Rosé and more). Live music on Fridays. Open until 7pm Saturdays.
- Mengler Family Wines — overlooking the Town Green fountain, live music Saturdays 1–6pm. Double-gold Unoaked Chardonnay.
We’ll grab dinner somewhere in Windsor or Santa Rosa (suggestions welcome).
Hotel
We’ll check in as a group and split rooms. Hampton Inn Windsor has a pool and hot tub, is walkable to everything, and has run a SMART train promotional package. Other options TBD. Book your own room early — June weekends in Wine Country fill fast.
Sunday
Getting Home
We’ll ride the SMART train south to Petaluma for a 10/10:30am Sol Food brunch (151 Petaluma Blvd S). Puerto Rican food, outdoor seating, opens at 10am — order the Pollo al Horno and a Cubano and do not skip the plantains.
After brunch, we ride. The route home is ~46 miles north-to-south, crossing the Golden Gate Bridge and finishing at 4th & King Caltrain:
Expect mostly flat terrain with some rollers through Marin County.
Logistics at a Glance
| Leg | Mode | Notes |
|---|---|---|
| San Mateo → SF | Caltrain | Bikes OK, no reservation |
| SF → Larkspur | Golden Gate Ferry | Bikes OK |
| Larkspur → Windsor | SMART train | Bikes OK, $2/bike |
| Windsor → Petaluma | SMART train | Morning, check schedule |
| Petaluma → 4th & King | 🚲 Bike | ~46 miles, Golden Gate Bridge |
A Few Notes
- SMART train schedule: Weekend service currently ends around 9–10pm — plan your dinner accordingly or be prepared to stay flexible.
- Bike requirements: Any rideable bike works for the transit legs. The ride home is 46 miles on pavement — drop bars not required, but you’ll want something comfortable.
- Packing: One bag. This is overnight but not a camping trip. You’re on a bike.
- Costs: Caltrain (~$6–10), ferry (~$15), SMART (~$10–15 each way) — roughly $40–50 in transit round trip. Budget for a hotel room share + food/wine.
Want in? Fill out this interest form so we can get a headcount, match hotel buddies and coordinate logistics.