Santa Rosa's Railroad Square draws tourists, locals with its shops, eateries and nightlife

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Anchoring the west end of Santa Rosa’s historic Railroad Square district is the former Northwestern Pacific Railroad depot, a pillared stone building constructed by local stone masons in the early 20th century.

Yesterday’s narrow-gauge train is long gone, replaced by today’s SMART train, which stops right behind the depot. Commuters to Marin County hop on, while tourists hop off and spend a few hours in Railroad Square shopping, noshing, and snapping photos of the buildings, some on the National Register of Historic Places.

Buildings that once served as warehouses, canneries, macaroni factories, breweries and other turn-of-the-century enterprises now house small shops, antique emporiums, a wine tasting room, eateries and a few watering holes.

Want to explore Railroad Square? A good place to get oriented is the California Welcome Center and Santa Rosa Visitors Center in the train depot, where a small museum of old photos and memorabilia sets the scene of the historic district. Volunteers here are loaded with walking tour maps, brochures, souvenirs, and advice about the entire Sonoma County wine region and beyond.

Bordered by the SMART train, with a Marriott and a Hyatt Regency hotel on one side, and the AC Hotel by Marriott under construction on the other side, Railroad Square is entering a new era.

“We’re enjoying some new day-trippers from along the SMART train line, and look forward to visitors from San Francisco when the train is connected to the Larkspur Landing ferry terminal, within six months or so,” said Mike Montague, president of the Historic Railroad Square Association.

“In the meantime,” he added, “We are the same quaint, friendly neighborhood of restaurants and boutique businesses in wonderful historic buildings.”

Housed in a massive, circa-1920 brick edifice on Fourth Street, Whistlestop Antiques will be celebrating its 45th anniversary on Sept. 15 during the Santa Rosa Art & Antiques Fair. It’ll line Fourth Street and the block fronting the train depot. The free event will include a classic car show, food trucks, live music and numerous arts, crafts and collectibles vendors.

Inside the lofty, 10,000-square-foot halls of Whistlestop are vintage treasures to be discovered from more than three dozen dealers. Shoppers can find Bakelite jewelry, Native American handcrafts, model trains and toys, sports memorabilia, and furniture from every era.

“Besides our local browsers, we’re now getting a real boost in visitors, due to the SMART train. We call them our ‘train people.’ (They) are mostly retired, relaxed folks who have time to ramble around, shop, and eat and drink in our restaurants,” said Dee Richardson, store co-owner.

“We do expect an even more diverse demographic when the train connects to the San Francisco ferry, and soon when the new AC Marriott hotel opens,” she added.

Among a bevy of boutiques, Disguise the Limit Costumes on Fourth Street features crazy outfits, masks, wigs and makeup for merrymakers.

On the corner of Wilson and Third streets, Hot Couture has for three decades been famous for vintage clothing, hats, dresses and accessories from the 1920s through the 1970s. Its men’s aloha shirts are in high demand.

Just north, The Batcave Comics & Toys lures kids and comic fans into their basement lair; Old Town Furniture next door and Olde Towne Jewelers across the street, are popular stores.

Next door to Whistlestop, the Welfare League thrift store offers bargains on clothing, home goods, jewelry and decor. Proceeds help support local families in need.

After shopping, visitors can stop by Daredevils Barbershop for a hip haircut.

Across from the train depot, Flying Goat has long been a popular spot for locally roasted coffee and lattes. Visitors rarely find open seats here.

Hearty breakfasts can be found at Omelette Express on Fourth Street.

Meanwhile, locally sourced foodstuff, baked goods and exotic condiments and sweets are on offer at Miracle Plum, where Santa Rosa natives Sallie Miller and Gwen Gunheim also sell kitchen wares, grab-and-go lunches, wines, ciders and craft beers. Their mission is to “highlight items made locally, made by women, and made thoughtfully.” Food-oriented workshops, art shows, meetings of the cookbook club and sit-down dinners on the patio are often sold out.

As the sun sinks into the west and SMART train passengers head out of town, hotel guests and locals amble over to Railroad Square to the restaurants, bars and entertainment venues.

At Jackson’s Bar and Oven, creative artisanal cocktails such as “Let That Man Go” and “Stay in Your Lane” are on the bar menu, along with lobster rolls and wood-fired mussels. Sonoma County wines, local and international brews and a wide selection of eats are served until 10 p.m., and 11 p.m. on weekends. Those in the know order the calorie-worthy white peach cobbler and Nutella pizza before last call.

Visitors should check out the 400 different Scotch, Bourbon, Irish, American and Japanese whiskies available at Jack & Tony’s Restaurant and Whisky Bar, where smoked pork chops, sea scallops and hearty mac and cheese are favorites. The eatery is open every day until 10 p.m.

Two blocks north, the Arlene Francis Center for Spirit, Art and Politics puts on various shows. Visitors can catch a poetry jam, flamenco performances and drag, heavy metal, hip-hop and punk shows. The center, located in a former flour mill built in the 1890s, is a busy hub for local musicians and artists.

“AFC was where we often played and established our band in town. We always felt supported there, and appreciated the commitment to bridging across all disciplines, backgrounds and ages,” said Melati Citrawireja, base player for the band Hose Rips. “There’s no one ‘scene’ here. Everyone comes!”

Another regional performing arts center, in a circa-1888 cannery building, the 6th Street Playhouse holds forth with professionally produced plays and musicals. Recent sellouts include Gypsy, Sweeney Todd, Shakespeare and To Kill a Mockingbird.

On Fridays, visitors can listen to soft jazz while sipping Sonoma County wines and sitting on the sofas by the fireplace at 4th Street Cellars. Open until 9 p.m. on weekends, the wine bar and tasting lounge is located in a 110-year-old building.

Nearby on Adams Street, the elegant bar at Stark’s Steak & Seafood has won numerous “Best Happy Hour” awards. The restaurant serves sustainable seafood, and Angus and American Kobe beef for lunch and dinner.

Later this year, owners Mark and Terri Stark plan to open a new place, Grossman’s New York Style Deli, Bakery & Bar, in the Hotel La Rose. Recipes are being perfected for house-baked bagels and house-cured pastrami and other deli favorites. They also plan to offer outdoor dining.

“We’re experiencing a renaissance of sorts in Railroad Square with the influx of tourists,” said Richardson, the Whistlestop Antiques co-owner.

She said bright posters soon will be displayed on windows, offering a “welcoming introduction to the district” and “showing a self-guided, historic walking tour route.”


Santa Rosa’s Railroad Square

Planning a visit to Santa Rosa’s historic Railroad Square? Here are a few places to eat and stay.


La Gare

Address: 208 Wilson St.

For four decades it has offered classic French cuisine in a romantic, Old World atmosphere. Guests will find on the menu chateaubriand, beef Wellington, escargot and cherries jubilee, as well as California and French wines.

Details: 707-528-4355;

LoCoco’s Cucina Rustica

Address: 117 4th St.

Visitors will find linguine di Mare, risotto, ravioli, lasagna and more traditional Italian favorites in a lively, casual trattoria.

Details: 707-523-2227;


Hotel La Rose

Address: 308 Wilson St.

This landmark hotel dates back to 1907. Located across the street is its contemporary-style annex, the Carriage House.

Details: 707-579-3200;

Hyatt Regency Sonoma Wine Country

Address: 170 Railroad St.

The 253-room upscale, contemporary resort offers a pool, fitness facility, restaurant, café and bar.

Details: 707-284-1234;

Courtyard by Marriott Santa Rosa

Address: 175 Railroad St.

The mid-scale hotel features 138 rooms, a gym and pool, bistro café/bar and meeting rooms.

Details: 707-573-9000;

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