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While many of us think of the ride to Pleasanton as a nasty commute and weekend excursions eastward as much more pleasant, Pleasanton, in fact, has a rather charming Main Street, complete with the old arched lighted white sign overhead, antique stores, and ye old tack shop. 

I remember Pleasanton as a place my parents used to drive me through on the way to Livermore swim meets. We would never actually stop there! 

Now it’s worth the trip. Located about seven miles west of Livermore in the Amador Valley where elk, grizzly bears, cougars, salmon, coyotes and reptiles once roamed, the area was first settled 4,000 years ago by the Ohlone, who called themselves The People. Native settlements on Pleasanton Ridge and on the lagoon were part of the largest concentration of Native Americans in North America. 

Mission San Jose de Guadalupe in Fremont, the 14th California mission, was founded on June 11, 1797 by Father Lausen, the second successor to Father Junipero Serra as the president of the missions. Lausen’s people raided the Ohlone and took their land as the mission’s pasture in the Alizal area to raise cattle for tallow and income for the mission. 

After Mexico won its independence from Spain, the Secularization Law supposedly meant Mexican citizens would share the land with Native Americans, but it never happened. In the late 1830s, most of Alizal land, as Pleasanton was called, had been granted to Mexican politicians and soldiers as part of the Rancho el Valle de San Jose land grant. 

In 1867 the name was changed from Alizal to Pleasanton, the misspelled effort of pioneer John Kottinger to name it after Civil War General Alfred Pleasonton. 

Eventually Amador Valley became an agricultural center with the oldest horse racing track in the United States, and farmers grew hops here sold throughout the U.S. and Europe to make fine beers. Because of Pleasanton’s Old West Main Street, Rebecca of Sunnybrook Farm with Mary Pickford was filmed in Pleasanton, making it temporarily “Hollywood of the North.” 

The first housing boom followed the railroad’s arrival in 1869. Successive growth spurts since the 1960s led to development of tract housing, large malls, strip malls, and industrial complexes, all leading to the neglect of downtown. Just in the nick of time, local historians helped revitalize downtown, and the average detached three-bedroom house now sells for nearly $830,000. 

Charles Bruce was the only real architect in town, but many builders bought plans from designers “back east.” The Amador–Livermore Valley Historical Society offers two excellent pamphlet guides to identify historic buildings as you stroll or roll Main Street.  

Once the site of the local Women’s Club, City Hall, the Police Station, and then the Library, the Historical Society Museum is worth the trip, with rotating exhibits, including “The Wonder Years: Pleasanton in the ‘50s and ‘60s” beginning Oct. 2. The Town of Pleasanton still uses the vault in a back room to store important historical papers, and the museum has 6,000 archived documents available to the public. 

Two doors north of the museum is an old fashioned Christensen’s Western & English Wear, with Tack Room, Saddlery, and Remedies, and everything the real or wannabe cowpoke could want. 

The Wine Steward and Wine Bar, supposedly the largest wine shop in the East bay, offers 50 of Kermit Lynch’s wines, local boutique wines from John Christopher Cellars, Darcie Kent, and Wood Family wineries, 60 wines under $10, and different themed tastings each week. Expect to be greeted by Bruce the border collie-malmut mix or Haley the Jack Russell yerrier, who playfully guard the A.G. Ferrari pastas and sauces. 

The historic Pleasanton Hotel has a nice restaurant, and Main Street is lined with several Italian, Mexican, and nouveau Californian restaurants, with local or chain coffee houses and bakeries interspersed.  

Pleasanton hosts its annual Antique Fair on Saturday, Oct. 10 on Main Street. 

Kids will love the water slide in the 296-acre Shadow Cliffs Regional Park just east of town on Stanley Boulevard, which also offers an 80-acre lake with trout fishing, hiking, and picnicking. Rowboats, electric motorboats, and paddle boasts can be rented year round, and bait and tackle are available at the boat house. Shadow Cliffs is a former gravel quarry donated to the East Bay Regional Park District by Kaiser Industries.  

Pleasanton Ridge Regional Park off Foothill Road in Pleasanton is the beginning of a planned Ridgelands Regional Park stretching to Kilkare Canyon, Sunol Ridge, and Stoneybrook Canyon. Because of the park’s multi-purpose trail system, the park is great for hiking, riding horses, cycling, and just meditating over the almost clear canyon streams and views.