Six years ago, I interviewed Cyndy and Jerry Oliver about the new shop they had opened at a prominent Winthrop location. Since then the Olivers have poured thousands of cups of coffee, cut hundreds of yards of quilting fabric, and hosted countless birthday parties, baby showers, and meetings. Now, 3 Bears Café and the 4 acres it sits on are poised for new ownership, as soon as the right buyer comes along. (The full business name is 3 Bears Café & Quilts. “The property and restaurant are for sale,” says Cyndy by way of explanation. “But I’ll move the quilt shop somewhere else at some point.”)
Although some may find the Olivers’ timing of listing the business mystifying, Cyndy says it was always part of their five-year plan when they began envisioning 3 Bears Café & Quilts. With the goal of selling after five years, the Olivers developed the property, which they bought in 2008, very strategically. “The permitting and infrastructure are in place to support an expansion,” Cyndy says. “We didn’t build on the main part of the property. We intentionally designed the carriage house and restaurant to be more subdued, so that whatever an eventual new owner wants to do with the property, the existing structure will be complementary.”
The five-year plan turned into a bit more than that due to the age-old “we just didn’t get it done” defense, and then almost immediately after the Olivers got the business and property ready to sell, the severity of the global pandemic was finally realized. “But,” Cyndy says philosophically, “we’re ready to sell, ready for someone else to take this place to the next level of ownership.”

Jerry and Cyndy Oliver: following a plan.
If that takes a while due to the coronavirus outbreak, so be it, says Cyndy. But a long wait seems unlikely, given the robust interest already expressed in the business. Potential buyers of 3 Bears Café & Quilts have been widely varied in their visions for expansion, Cyndy says. “People have had ideas about vineyards and tasting rooms, whiskey bars and steak houses, bed and breakfasts — there have been so many ideas.”
“When we built, we knew that each prospective future buyer would put their own spin on what they do,” says Cyndy, “and we tried to envision all the different uses.” For example, Cyndy notes that the back of the property has room for three cabins (which I would hope would be named Papa Bear, Mama Bear, and Baby Bear) and that the conference room upstairs is equipped with a dumbwaiter, for someone wanting to develop a full-size restaurant. “We have that foodservice niche already established too,” Cyndy says, “so it wouldn’t be hard for someone to scale that up. The property is very developed in terms of a solid foundation, so it will be pretty easy for a new owner to hit the ground running.”
The Olivers have been surprised by the number of international visitors who have visited the café over the years. “One of the things that surprised me the most was how many international travelers we get here,” says Cyndy. “I had no idea. But we’ve had customers from Germany, Switzerland, Africa, Norway — all over the world.” The visitors sit on the patio, Cyndy says, which overlooks the river, and they say “So much of America is fast-paced. But here you can sit and relax. It’s a pause from America’s pace.”
The idea of selling the business and property is bittersweet. Cyndy says. “It’s been one of my favorite jobs ever. We bake things from scratch, I love helping people with quilting plans, and it’s been wonderful to meet new people and connect with locals.
But Cyndy says she knows “something neat” will happen under new ownership, something that will contribute to the community. “And,” she says, “we will be right there to help get them off to a good start.