Various downtown locations will become tasting rooms on Saturday, May 4th On Saturday, May 4th from 5-8 pm, Pleasanton's Annual Wine Stroll will turn various downtown locations into tasting rooms. Guests will have the opportunity to spend a beautiful evening in downtown Pleasanton, sampling wine from local wineries that will be paired with tasty bites. Additionally, there will be live artists and musicians performing throughout Main Street.from 5-8 pm for Pleasanton's Annual Wine Stroll. Guests will spend a beautiful evening in downtown Pleasanton sampling wine from local wineries paired with tasty bites. There will be live artists and musicians performing throughout Main Street.