Phoenicia Diner owner buys Gypsy Wolf property

Michael Cioffi at the Phoenicia Dinner. (photo by Dion Ogust)

Michael Cioffi at the Phoenicia Dinner. (photo by Dion Ogust)

Michael Cioffi, who speaks on this week’s Woodstock Chamber of Commerce & Art panel discussion on “The Changing Face of Woodstock,” has been best known up to now for his turnaround of the Phoenicia Diner, which has been pegged as the best of its kind by a growing number of websites and hipster publications. But for Thursday’s intent and purposes, he’ll be more aptly presented as the new owner of the site of the late Gypsy Wolf Restaurant out Tinker Street towards Bearsville.

“I purchased the building and half the property it was on, about one acre, about a month ago,” said the former New York-based television and movie set builder who still bases himself and his family in Brooklyn. “Miller Howard kept the back property for their own building purposes. As for what my plans are…I’m just getting everybody I work with starting to figure out what would make sense, what would fit the town right now.”


Cioffi says he hadn’t even worked in a restaurant before buying the old 1962 diner on Route 28, which had been in Phoenicia since the early 1980s, a few years back. But he knew enough to recognize that who you hired was important. So he brought in Mel Rosas, of Sweet Sue’s and Bread Alone, as chef. Then some veteran wait staff.

Now he’s realizing, as a start for his new Gypsy Wolf concept, that doing a diner wouldn’t make sense because it would eat into his current success. Similarly, he’s not so sure Mexican food would work any more, given the success of the Tinker Street Taco Lab, and imminent arrival of Santa Fe, of Tivoli and Kingston fame, to the old Maverick/Black Bear restaurant site next to the new Hotel Dylan on Route 28 in the coming months.

“We also have to figure out what to do at the site,” he added, noticing how the Gypsy Wolf building, stripped of its popular decorations and paintings, “looks like a shack” and is on “something of a threshold.”

Cioffi said his penchant, as at the Phoenicia Diner, is to “enhance and embrace what’s there” and treat his investment as “an opportunity to update things a bit.”

He added that he’s been roundly welcomed by everyone he’s been meeting and speaking with in Woodstock, both in terms of its government and business community. And he fully realizes the strength of the Gypsy Wolf’s location, what with parking and The Bear Cafe down the road, as well as his own new role as a “restaurant concept kind of guy” — something he still finds somewhat astounding, given his newness to the field.

“I like that the building has history, and Woodstock seems to be an interesting time right now,” Cioffi added. “We’ll take our time getting this right…I certainly don’t want to lose any focus on the diner.”

He paused and noted how he’s also been getting requests to do something out in Margaretville, where he’s kept a second home for decades. Then continued.

“Staffing will, of course, be a big part of what we do,” he added. “We’ll take a couple of months to see what the town wants, and needs, just as we did out in Phoenicia.”

He asked that we check back with him in the new year.

“In the meantime, I’ll have to figure out something to include into this discussion,” he concluded.

That panel discussion, “The Changing Face of Woodstock,” will also include James Conrad, new co-owner of The Golden Notebook and the panel’s moderator, Annemarie Gilly, COO of Miller Howard Investments; Lisa Halter of Halter Associates Realty, Neil Howard, new owner of The Colony, Jess Walker of Walker Architecture and Michael Lang. It starts at 6:15 p.m. Thursday, October 22 at the Woodstock Golf Club’s Creekside Grill. See for more info…and needed reservations.

There are 9 comments

  1. Julie Houska

    I’m not a business person, and this is probably just a pipe dream, but I wish, and I’m sure I’m not alone in this, that they’d replace the public pool that used to be there when it was known as “Swim-O-Links.” I’ve lived in this area my whole life, and I know that many in the community would be SO happy to see that happen! It was a sad day when it closed down, and even a sadder day when it was filled in. Of course, I’m aware that there would be a certain amount of liablilty issues, but if it’s done right, I’m sure that it would attract ample revenue, not only from Woodstock residents, but also from neighboring towns. I know that the pool would be “seasonal,” but perhaps they could raise the old Gypsy Wolf building and build a bowling alley, which would be a year round business. As a life-time resident, I also remember when the building which is across the street from the Overlook Methodist Church on Rt. 212 was a bowling alley. We had a lot of fun there back in the day! I think it’s about time to bring back some businesses to this town, other than restaurants, which would provide the community with something fun to do! Like I said, it’s probably just a pipe dream, but I’m sure I’m not alone in my dream…

  2. AMG

    Whatever it ends up being, I’m hoping it’s a comfortable, accessible place with great energy and affordable prices. We have enough of the poncy, over-priced eateries in the Woodstock area. Good luck, Mike!

  3. Kate Miller

    Cafeteria! The kitsch value is high and I think we are ready to revisit this concept. I live a little over a mile from the GW site and would love to be able to zip in, pick up a solid non-GMO, healthy dinner (or three) in an earth-friendly biodegradable container for around $12ish. I do this with Bistro-to-go occasionally but it is a bit of a schlep… eat in cafeteria with an easy pick up–that would be great.


    I live less than 1000ft from the GW and would like to see a ”diner” with organic and non gmos but affordable enough for locals and tourist .There maybe room for outdoor eating and even outdoor concerts if the driveway is paved or at least partly dust free.As a local i always here people complain theres not enough down home affordable local healthy food choices.I used to go to the Black Bear several times a week when i was still working,great food and great prices.You know food ,Mixed with music and a Bar and Theres room to expand if Biz does all right .Its a unique Woodstockish Bldg,but small but that maybe an advantage.Whatever you do i wish you the best in all your ventures and i will definetly be a regular and in walking distance,That sure works for me,need help ?

  5. Donna

    Whatever you decide, make it affordable for the local people as well as the weekenders. I think a diner that is not too expensive would be a great addition to the Woodstock dining scene.


    I think that it is exciting that Mike will be bringing new energy to town,Hopefully it will be a restaurant that will be open late on Saturday so that there will be a welcome environment for after evening Maverick concerts.

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