We were always fans of Hope and Olive, but since we moved here last year it’s become our favorite downtown Greenfield restaurant to take visitors. It’s the perfect first night in town experience. The food is locally-sourced and consistently excellent, it’s close enough to walk, and the vibe is as personal as preparing dinner for friends in your own kitchen.

Hope and Olive feels like home

I think a lot of people in the area feel that way. I recently sat down with two of the owners, Maggie and Jim Zaccara. Together with their friend Evelyn Wulfkuhle the siblings opened Hope and Olive in 2007. I spoke with Jim about the restaurant’s history and what he thought contributed most to its unique sense of place.

Jim is a familiar face to anyone who dines at Hope and Olive. “Basically, for the last ten years, I’ve lived here as much as I’ve lived at home.” His commitment shows. He’s usually the one to greet you at the front door and he still manages to somehow be everywhere at once as you dine. It’s not just that he’s on top of things. There are plenty of restaurateurs who work hard. What’s unique is that he and his staff make you feel so welcome too.

The Secret of their Success

Overall Greenfield is a sleepy little town. Despite that, Hope and Olive stays busy, every day but the Monday they’re closed. I asked Jim why he thought the restaurant resonated so well with people in the area. He mentioned the diverse menu, and reasonable price point, but what he said about his staff and overall philosophy captured it best for us.

“I like to hire people who are genuine personalities, who get excited about giving people a good time. I intentionally instill in the staff, be who you are with your customers, don’t put on a performance. That’s what I want when I go out. I want to have a real experience with people.”

Three years after Hope and Olive opened in 2007 its sister restaurant, Magpie followed. Magpie specializes in wood-fired pizza, creative cocktails, and delicious tapas-style appetizers. Before either of those two favorites though, the brother and sister team opened Shelburne Falls’ A Bottle of Bread in 2000. It remained a local darling until 2005 when it closed, sadly, after a fire destroyed its kitchen.

The owners take giving back to the community even farther than serving farm to table

It was at A Bottle of Bread they held their first benefit, for Natural Roots Farm, a local cooperative in Conway. The event went over so well they held more. The tradition evolved into Free Soup and Game Night at Hope and Olive. These regular benefits are held the first Monday of every month but July and August, and help local nonprofits that don’t necessarily attract a lot of attention or funding. A core group of staff volunteer their time, and help source the list of beneficiaries.

Deep Restaurant Roots

Jim and Maggie’s restaurant history goes back even further than A Bottle of Bread. Along with their 8 siblings, the two grew up in the restaurant world of their father, who owned a Chuck’s Steakhouse in Connecticut. Chuck’s was a franchise born in the seventies, what Jim described as a Mad Men type place that boasts it invented the modern salad bar. The entire Zaccara clan worked there as kids, and the love of restaurants stayed with many of them after they moved out on their own.

In addition to Jim and Maggie’s two restaurants, one of their sisters owns The Wagon Wheel in Gill. If you haven’t made the trek, you should, it’s worth it for the homemade ice cream and ridiculously decadent signature pancake alone (check out the description on their site!). A 4th brother owns The Bull’s Bridge Inn in CT.

And the food!

All of the charm would be wasted of course, if the menu wasn’t as inventive and delicious as it is. While Jim is also a cook, Maggie attended the New England Culinary Institute and is the mastermind behind the menu. She isn’t your stereotypical tyrant in the kitchen though. The menu changes, “three, three and a half times a year,” depending on what’s in season, and she encourages input and ideas from her staff.

One of our favorites right now is a salad called the The Lobster Louie, a sort of Cobb-Wedge mash-up with greens, egg, avocado, pickled onion, tomato, green beans all tossed in house-made Russian. I also love two takes on classic Mediterranean dishes, a Fattouche salad and a kind of deconstructed Lamb Tagine that includes quinoa, roasted chickpeas, almonds, and a cucumber salad.

Check out some images of other great menu items at the moment.

If you haven’t tried Hope and Olive, we couldn’t recommend it more strongly. Weekends can get busy, but it’s well worth the wait. And don’t forget they’re closed Mondays. If you do forget, you can always walk a block over to Magpie!