Weekend itinerary
Cypress Creek sets the pace here: a cold morning swim at Blue Hole, a slow loop of the square, and a creekside porch waiting after dark.
By Cal Mercer — a Second Star Guide itinerary
Reserve Blue Hole first, then fit Wimberley Square, Old Baldy, and current Jacob's Well hiking access around that half-day session.
Best length
2 nights
Two nights leave room for a reserved Blue Hole half-day, the square, Old Baldy, and one current-status natural-area visit.
Stay
Hotel Flora and Fauna
A boutique hotel near central Wimberley with a pool and individual rooms.
Main activity
Blue Hole
Blue Hole owns the reserved half-day; the square, Old Baldy, and current Jacob's Well hiking access fill the remaining windows.
Pace
Slow-town weekend
Good for couples and small groups who want the place itself — food, history, water, storefronts, and after-dark glow — to matter as much as the headline stop.
Friday
Use Friday for the lodging check-in, Wimberley Square, and a current restaurant. Keep the evening close to town rather than adding another outdoor drive after dark.
4:00 PM
A boutique hotel near central Wimberley with a pool and individual rooms.
Recommended stay
A boutique hotel near central Wimberley with a pool and individual rooms.
Check availability
Upgrade
A bed-and-breakfast on Cypress Creek with guest rooms, cottages, and spa services. Confirm the room type and current creek-use rules directly with the property.
Compare the upgrade
6:30 PM
Wood-fired pizza, craft beer, cocktails, and outdoor seating accommodate casual family meals and group gatherings.
Saturday
A morning Blue Hole reservation leaves the afternoon for the square and Old Baldy. An afternoon reservation reverses that order.
8:30 AM
This long-running café on Wimberley Square serves breakfast and lunch near downtown shops.
10:00 AM
Bring the reservation confirmation, check the city's swim-season banner and water-quality page, and arrive for the published half-day session.
2:00 PM
After Blue Hole, return to the lodging for dry clothes or continue to Wimberley Square. Save Old Baldy's exposed stone steps for cooler temperatures.
7:00 PM
Hill Country-inspired cooking and creekside tables set the scene for a relaxed dinner after exploring Wimberley.
A full-day electric-bike rental for Wimberley roads and the town center; verify the operator route, current availability, and road comfort before booking.
Sunday
The last morning should keep the spell intact: pastry, coffee, a quiet street, or one more look at the water before the road takes over.
9:00 AM
Start at Wimberley Cafe, then choose Old Baldy or Jacob's Well Natural Area if the county alert and departure route support the stop.
11:00 AM
Old Baldy offers a short exposed climb and Hill Country view. Jacob's Well offers trails and the spring overlook, but swimming remains closed under the latest alert.