Restaurant openings point to business revival in Chester

By Shawn Cunningham
© 2025 Telegraph Publishing LLC

As the days turn colder it seems the business climate in Chester is heating up with around a dozen businesses opening, moving, expanding or changing hands in industries as disparate as restaurants and livestock farming, home decor and childcare. And with all that, a number of prominent local buildings are getting spruced up.

In the first in a three part series on the changes we look at news in the town’s restaurant/hospitality sector.

Less than two weeks ago, the long-awaited restaurant connected to the Meditrina Wine and Cheese shop began soft openings, holding dinners for small numbers of customers to fine tune its menu and service. Now its open for business. Owners Justin and Amy Anderson have been talking about having a wine bar since May 2018, when they moved their eight-year-old wine shop near the Chester Post Office to the Main Street building that once housed the Moon Dog Restaurant.

They knew that since the closing of The Free Range in 2020, the demand for another full-service restaurant was high as people consistently stopped by to ask when theirs would open, but progress was slow. It was February 2024 when the transformation began in earnest as Justin left the wholesale wine business to concentrate on building out the new venture.

And, as with so many business stories these days, the shortage of contractors and inspectors slowed progress. But with help from friends, the couple transformed the old space into a new dining room, bar and kitchen while moving the wine shop to the rear.

In early October, as the finishing touches were coming into focus, Meditrina announced that Nevin Taylor of Bliss Farm would be the restaurant’s executive chef.

The menu features small plates — such as marinated mussels, ricotta crostini and crab toast — for sharing, pizza, pastas and olives and almonds.  The Andersons say the place is inspired by their travels in Europe and a life in wine and food and they want the atmosphere to be “more chill” and focus on family, friends and food.

“And a kick ass wine program,” adds Justin.

Alder Bakery & Eatery

Across town, Andover resident Miguel Calderon is planning an opening of his own while he and his wife Kirsten work to give the former Heritage Deli and Bakery a facelift and update the kitchen as well as the offerings.

The Alder Bakery & Eatery will start out offering breakfast and lunches when it opens late this fall.

The Heritage, a restaurant much loved for its baked goods and hearty meals, closed when owner Michele Wilcox decided to retire after 23 years in the business.

Calderon, who has worked in the industry for more than a decade and worked or interned at Michelin star restaurants in New York and Chicago, says they plan to focus on the bakery with tarts, croissants and other pastries. He plans to serve up some with echos of his Puerto Rican heritage, including a guava-filled puff pastry. Breakfast sandwiches, French toast and omelettes are among the offerings to round out the morning meal.

Later next year, the couple will begin offering dinner with a casual atmosphere and shared plates like tapas. Calderon says it’s important to him that they serve really good food at prices that locals can afford. One aspect of this is coffee. Calderon had been on the hunt for the best coffee he can find to serve to customers at a reasonable price, and recently found that vendor in Intelligentsia coffee.

“This will be a locals place first,” says Calderon, a Florida native whose local connection comes through his in-laws in Andover, who run Abundance Acres, a CSA farm and gathering place. Once in the area he began to work as a private chef and caterer sometimes traveling with his clients, but he admits he had his eye on the Heritage for a while.

With fresh paint inside and out, new flooring and a change of layout, the Calderons expect that Alder will be familiar enough to attract The Heritage’s regular customers, while bright and modern enough to draw in new clientele.

Much like Wilcox did for special events, the Calderons also intend to utilize the land behind the restaurant. However, the Calderons are planning to build a three-season pavilion with a wood-burning oven perfect for pizza.

At last check, the flooring was about to be installed making it possible to get on with finishing the interior. In an Instagram post Miguel Calderon said there is the potential for opening by the end of November, but “with so many moving pieces we are remaining flexible and positive!”

Springfield Regional Development connection

What both the Andersons and Calderons have in common is the help of Springfield Regional Development in business planning and with loans. SRDC Executive Director Bob Flint works with prospective as well as veteran business owners to focus their plans and find the funding to carry them out.

In the case of Meditrina and Alder Bakery, Flint made sure their plans and numbers worked before lending them $55,000 and $32,500 respectively from Regional Development. He also helped them present their plans to the Chester Select Board when applying for loans of similar amounts from the Chester Economic Development Fund.

“I was very impressed with how careful and thoughtful Miguel was in his business planning and pragmatic in how he approached the project,” Flint told The Telegraph, “I hope he gives the property a new life for Chester.”

Flint also said, “I’m so proud of Justin and Amy. They showed perseverance in working through challenges and will now have a great dining option on the Green.”

On Tuesday Town Manager Julie Hance told The Telegraph that “We are thankful to Bob and SRDC for the service they provide in helping us vet applications for economic development funding.”

Future expansion and possible change of hands

While not a brand new spot, after about six months in business, the Cafe at Sugar Bob’s on Route 11 West — in the cathedral-like former home of Baba a Louis Bakery  — will get a chance to expand its seating when Collected Ltd., the locally owned antiques and home decor store, moves to its new digs.

The Cafe at Sugar Bob’s is open every day from 10 a.m. to 5 p.m. with coffee and espresso drinks. There’s also a variety of sweet and savory baked goods, soups, chili, salads, wraps and even pizza by the slice. It’s an extension of the production facility of Rob Hausslein’s Sugar Bob’s Finest maple products lines.

The Fullerton Inn will be going up for auction between Nov. 6 and 13. If an acceptable bid is made, Chester’s restaurant scene may change again in the coming year.

This is Part 1 of a three-part series on Chester’s Rising Business Scene. Next week: Retail businesses grow.