Pleasanton

Pleasanton sits in the Amador Valley on the far side of the East Bay hills, about 32 miles from Palo Alto. It is a prosperous suburb of about 80,000 people and home to the headquarters of Safeway, Workday and Veeva Systems. The Census Bureau ranked it the wealthiest middle-sized city in the country in 2005 and 2007.

What makes Pleasanton worth a trip is its old downtown. Main Street keeps a run of buildings from the 1800s, a small free history museum and a Saturday farmers market. The Alameda County Fair fills the fairgrounds every summer. The hills and parks around town offer hiking and a swimming lake. This guide covers the trip from Palo Alto, the history, the sights and how to plan a day.

Where Pleasanton is and how far

Pleasanton is in eastern Alameda County, in the Tri-Valley with Dublin, Livermore and San Ramon. Interstate 680 runs along its west side and Interstate 580 along its north edge, where the two freeways meet. Pleasanton Ridge rises to the west and the Arroyo Valle and Arroyo Mocho creeks drain the valley floor. Summers are much hotter than in Palo Alto; the city's record high is 115°F.

From downtown Palo Alto it is about 32 miles. Outside rush hour the drive takes 35 to 45 minutes.

Getting there from Palo Alto

By car

The most direct route crosses the Dumbarton Bridge, follows Route 84 through Fremont and joins Interstate 680 north over the Sunol Grade. The bridge toll is charged only westbound, on the way home: $8.50 in 2026, $9.00 with FasTrak from January 1, 2027. To skip the bridge, drive around the south end of the bay on Route 237 and take Interstate 680 north from Milpitas. Our East Bay travel guide compares the routes.

By BART

Two BART stations serve the city along its northern edge: West Dublin/Pleasanton beside Stoneridge Shopping Center and Dublin/Pleasanton at the end of the line. On weekdays, take the Dumbarton Express from Palo Alto to Union City BART, ride north to Bay Fair and change for a Dublin/Pleasanton train. On weekends, ride Caltrain to Mountain View and VTA light rail to Milpitas BART instead. Either way, allow close to two hours.

By ACE

The Altamont Corridor Express stops at Pleasanton station near downtown. Trains also stop at Santa Clara and Great America, a short trip from Palo Alto. ACE runs four round trips on weekdays only, heading toward San Jose in the morning and back toward Stockton in the evening. That suits an evening trip out and a morning return better than a day trip.

From Alisal to Pleasanton

Ohlone people who spoke the Chochenyo language lived in the valley for thousands of years. In the 1770s about seven tribal groups, perhaps 2,000 to 2,500 people in all, lived in villages of 60 to 90. The first Spanish expedition arrived in 1772. Many valley people later joined Mission San Jose after its founding in 1797.

In the Mexican era the land became part of Rancho Valle de San Jose, granted to the Bernal family and their relatives Antonio Sunol and Antonio Maria Pico. The neighboring Rancho Santa Rita covered the rest. An early settlement called Alisal grew up around the adobe of Francisco Solano Alviso, built in 1844 and one of the oldest houses in the valley. It still stands in Alviso Adobe Community Park. In the Gold Rush years Alisal had a rough reputation as a hideout for bandits.

In the 1860s the justice of the peace John W. Kottinger, who had married into the Bernal family, named the town for his friend General Alfred Pleasonton of the Union cavalry. A clerk's spelling error in Washington, D.C., is said to explain why the town is Pleasanton. It incorporated on June 18, 1894. Mary Pickford filmed Rebecca of Sunnybrook Farm here in 1917. Phoebe Apperson Hearst lived on a large estate in the hills, the Hacienda del Pozo de Verona, later remodeled by Julia Morgan; it burned in 1969 and its site is now a country club.

After World War II, farms gave way to subdivisions. From the early 1980s, business parks such as Hacienda Business Park brought corporate headquarters.

Main Street and Museum on Main

Downtown Pleasanton is one of the best preserved small-town main streets in the Bay Area. Buildings in Gothic Revival, Italianate, Colonial Revival and Queen Anne styles stand within a few blocks. The Kolln Hardware building at 600 Main Street, with its five-sided corner tower, was built in 1890 for a hardware business. A 1990s redesign of Main Street favored pedestrians and outdoor dining.

Museum on Main, at 603 Main Street, tells the story of Pleasanton and the valley. It is open Tuesday through Saturday from 10 a.m. to 4 p.m. and is free, with donations welcome. A farmers market sets up on Angela Street, just off Main Street, on Saturday mornings. In summer, the downtown association has traditionally held free Friday evening concerts in Lions Wayside Park. Our farmers markets guide covers Palo Alto's own markets.

The Alameda County Fairgrounds

The fairgrounds, a short walk from Main Street, host the Alameda County Fair each summer. The first fair was held in October 1912. The 2026 fair ran from June 19 to July 12, open Wednesday through Sunday from noon to 11 p.m. plus Juneteenth and July 4, with rides, livestock, concerts and food. Its one-mile racetrack dates to 1858 and is often described as the oldest of its kind in the country. Through the year the grounds host trade shows and events, including the Scottish Highland Gathering and Games on Labor Day weekend. Check the fair's website for the 2027 dates.

Parks and the hills

Pleasanton Ridge Regional Park covers the oak and grass ridge west of Interstate 680, with more than 25 miles of trails, mostly old ranch roads, climbing from about 400 feet at the main entrance off Foothill Road to more than 1,600 feet. The park grew after residents defeated a plan for homes and a golf course on the ridge in 1983. The Tyler Ranch Staging Area opened in December 2023. Go early in summer; there is little shade.

Shadow Cliffs Regional Recreation Area, on Stanley Boulevard at the Livermore border, is a former Kaiser gravel quarry that opened as a park in 1971. Its lake has a sandy swimming beach with lifeguards in summer, fishing with a park district permit and boating. The district tests the water and sometimes closes the beach. For more hiking, Sunol is a short drive south.

Food and shopping

Main Street and the blocks around it hold most of Pleasanton's independent restaurants, from casual cafes and bakeries to wine bars and dinner spots with patios. Stoneridge Shopping Center, the regional mall, sits by the West Dublin/Pleasanton BART station. Livermore's wineries are 15 minutes east, so many visitors pair a Pleasanton lunch with tasting. Our Livermore Valley guide covers the wineries.

Why a Palo Alto resident might go

1. A walkable old downtown. Main Street and its museum make an easy, low-key afternoon.
2. The county fair. It is a classic summer fair within easy reach of Palo Alto.
3. Warm weather and a swim. When the Peninsula is foggy, Shadow Cliffs is usually sunny.
4. Wine country nearby. Stay over and taste in Livermore the next day. You can compare hotels in Pleasanton for your dates.

Frequently asked questions