Pleasanton, Calif., is — no surprise here — a pleasant small city east of San Francisco Bay that was off the beaten track for much of the 20th century and avoided the redevelopment that destroyed the cores of many older cities. Its downtown — filled with tree-lined streets, vintage architecture, restaurants and boutiques — evokes a small town in New England. My good friend Laura, who used to live there, was my guide on our trip. The tab: We spent about $450, including $220 for two nights at the Sheraton and $230 for food and drinks.
The Rose Hotel downtown (807 Main St.;  843-9540; rates from $240), an elegant beauty owned by the Madden family (John Madden, the former Raiders coach, raised his kids in Pleasanton), scores a touchdown. The old-world lobby has a marble fireplace, hand-painted murals and a dramatic staircase. The rooms are lovely, with rose-inspired fabrics and furniture; bathrooms feature whirlpool tubs. Alas, Laura and I were on a budget, so we stayed at the Four Points by Sheraton (5115 Hopyard Road;  460-8800) in the nearby business district, where we got a decent room for a great rate. Bonus: a nice pool in a lush setting.
With our hotel savings, we could eat our way around town, in between sightseeing. Breakfast: huge omelettes at funky Dean's Café. Lunch: fish and chips, and people watching, on the patio of Redcoats British Pub & Restaurant. Happy Hour: gyro sliders and Chardonnay at Oasis Fusion Grille. Dinner: grilled chicken breasts in a sauce of roasted figs, balsamic vinegar and pasilla chiles at the Blue Agave Club. Nightcap: Martinis at Hap's Original, a local hot spot.
The self-guided Historic Downtown Walking Tour (downloadable map) explores an architectural candy store of styles, ranging from Italianate to Mission Revival. Many buildings claim tales of ghost sightings, murder mysteries, secret tunnels, speak-easies and brothels. Some now house boutiques, and we had a swell time shopping along the way. Even the Round Table Pizza place has a storied history. It was built in 1863 as the Pleasanton Hotel, but it once stabled Seabiscuit and boasted an impressive list of non-equine guests: Henry Ford, Leland Stanford and Presidents Herbert Hoover and Calvin Coolidge. Bookstore lovers alert: Stop by Towne Center Books, a fine indie shop housed in a 1937 building that was once a laundry.
The lesson learned
Be sure to explore the side streets. We almost missed the new Firehouse Arts Center (4444 Railroad Ave.;  931-4850). The striking wood-and-brick building pays homage to the fire station it once was — there's still a fire pole — and has an art gallery and an intimate "black box" theater with amazing acoustics.