Throughout the years, Downtown Alpena has had many changes and shifts. However, there have been businesses that have lasted for many decades. These are businesses that continued to thrive even after having to change buildings and ownership, that continued to provide quality service to appreciative and loyal customers in their community. Luckily, there are quite a few of these businesses that are still open today.  

In this second post of the series, we are highlighting businesses that have remained involved in Downtown Alpena since around the 1920’s and sharing their perspectives on what changes have shaped our downtown over the years.

Alpena Agency, Inc. 

Since their opening in 1930, Alpena Agency has been a family owned and run insurance agency. Frank Bailey was the original owner of the agency and began it out of his home, spending his time going door to door to sell premiums and policies. Before coming back to Alpena, Mr. Bailey drove a cab in Detroit. He quit the cab business and moved into working in insurance. After a few years of walking and selling to the community, the agency expanded and moved officially to Downtown Alpena into an office that was located above where Cabin Creek Coffee is now. After serving in the Air Force as a fighter pilot in the Korean War, Frank Bailey’s son came to work with him. In the 60’s he took over. They switched locations to a building that used to be attached to PNC Bank, where their drive-thru windows now are. In 1972 they moved to their current location. They do the hard work and bring the best rates to the community of Alpena. Steve Wilson, the current owner and grandson of Frank Bailey, became involved in the agency in 1989. As their agency expanded, in 1992 they bought the old Jerry’s Printing that had been next door so that they could expand their office space. Around 1995, Steve’s brother, Pete, got involved and by 1997 he and Steve had bought the company and have been partners ever since. “We have people who buy insurance, and you have insurance companies, and we are definitely in the middle,” says Steve Wilson. They are truly a family-run company and are a wonderful part of connecting Alpena residents to their insurance needs. “We’re also a representative of the customer as an advocate in certain situations. We try to bring value through incredibly good service,” Steve says. 

Steve was on the DDA board many years ago and says that “downtown has come so far since the 90s; it was very institutional or stale looking downtown. There were empty buildings, and it just wasn’t a place where people wanted to go.” When he was on the board, it was the beginning of the changes that we see having been made today. “It changed from that to a spot that everyone wants to go.” In his opinion, some of the biggest changes have been the general look of Downtown Alpena. He was one of the driving forces for changing from a double lane to a single lane on 2^nd Ave, bringing more street-side parking into downtown. This was a kickstart to the beautification of downtown. “We’re not going anywhere, we like being downtown,” says Steve, and we hope they always stay.  

Bolenz Jewelry 

Walter Bolenz was a German immigrant who came to Alpena in the 1920’s. He began a career working for Besser Company. Alongside of his career there, he worked in clock and watch repair because that had been his training in Germany. In Alpena, he became known for his clock and watch repair expertise. During WWII, Besser became a defense contractor, and because Walter was a German national, he was demoted from his position as a foreman at Besser. He never forgave them for that, and after the war he started his own businesses. His first store was where JJ’s Steak & Pizza House is today. He had his business there from about 1947 to 1964 when he moved across the bridge onto 2^nd Ave in the block where Nicolet Bank is now. Before Culligan Plaza was created, that section of the block was all storefronts. He was there until 1979 when the city was planning to tear that block down to make Culligan Plaza and First Federal. At that point he moved to where Bolenz Jewelry is currently located. During that same year, Walter retired as he had been sick. He turned the business over to his daughter, Susan, and his son-in-law, Bob Adams, who both had been working with Walter from the 50’s on. From 1979 to 1992 they ran the store until Wayne Calkins and his wife bought it from them. They have been running it ever since. In 2001, Bolenz expanded, and they purchased the space next door that used to house the Michigan Consolidated Gas Company when that company moved out. They started out as just Wayne and his wife, and the next year they added one more employee and have slowly expanded since then.  

“I think that one of the big things that really, believe it or not, made a big difference is getting all of the apartments upstairs in Downtown Alpena. Little things like that have changed, and when people start living downtown it changes the dynamic,” says Wayne Calkins. “With the grant programs that the DDA was able to plug into to get money for renovations of all of these upstairs apartments, I think that made a big difference. Then, of course, gradually we got some new businesses coming in with younger people taking over businesses and I think that was important because most of the business owners downtown were aging at the same time.”  

Alpena’s growth has made a huge impact on downtown. “The biggest change for me personally has been the hotel; it seems to have turned us into more of a restaurant district and there has been a lot more foot traffic,” says Wayne. “Another difference that I’ve seen since I was here, and I think it’s very important, is that when we first started hiring people we would hire high school students and so on, and it seemed like they all couldn’t wait to get out of here, to leave Alpena. Now, the students that we have had the last 15 years, it seems like they want to come back. After they’re done with college, they’re looking for jobs to come back here. That never used to happen, but it’s not that way anymore. We seem to have changed the culture of what young people think of Alpena.” 

Masters Shoes 

The original owner and founder of Masters Shoes was an English immigrant named George Masters, the great grandfather of Jim Masters, the last member of the Masters family to own and run the business. He started the business with a man named Barrett, so the store was originally known as Masters & Barrett. Along with selling shoes, Masters & Barrett had a textile that they ran together. Over time, George Masters ended up just doing the shoe business and it was handed down to Claire Masters, Jim Masters’ grandfather. Claire passed the business down to Toby Masters who had originally been in the insurance business in Indiana but came back to go into the shoe business. Jim Masters graduated from the University of Michigan in 1963 and then was drafted, spending two years in Fort Polk, Louisiana. Afterwards, he joined his father and worked under Masters Shoes. In 2002, it became Masters and LaLonde Shoes when Jim Masters and Paul Detloff combined their businesses to give themselves and each other more time to enjoy their lives. In 2011, Masters and LaLonde Shoes was sold to Shawn and Steve Straley. Although the business closed in 2020, some of the remaining inventory remains at Alpena Furniture & Flooring, which Steve currently owns. 

“The shoe business has gotten more competitive than ever because big box stores, but I’m sorry to say that we’ve lost all our personal relationships that we had as individual retailers. Even today you look downtown and its changed, you don’t have major clothing stores, major shoe stores, major department stores, and you’ve got smaller facilities and its just a change in market but it’s too bad because you go into these larger facilities and you don’t get personalized care and someone waiting on you,” says Jim Masters.  

With the growth of chains and the desire for convenience, it can be easy to lose sight of what matters the most when working in a small business; the people you help that support your business. “Downtown was so successful for so many years, but I did see a lot of the established businesses close and many of them never had a replacement. Martinsons used to be on the corner, and they were a major clothing store, Tony & Norms across the street, Kennedy Jewelry, Woolworth’s, we had many facilities right on the main street.”

“I think the malls probably affected the change downtown more than anything, the general habits of the public changed with the malls as centralized districts. Online shopping is a tragedy for any retail business. Money is made here, and it should be spent here. If I wasn’t as old as I am I’d probably still be in the shoe business. To have more major merchants locate downtown instead of going into the malls and eventually going out of business, I think their lifelong existence would be better downtown than it would be in the malls. You can’t put a chain in, an individual has to have the desire to survive. Our family was involved forever in the shoe business, and it was really very beneficial.” 

Myer’s Fashions Etc. 

Myer’s Fashions Etc. did not start out as a women’s clothing store. Ellen Gould’s grandfather started the business and used to travel with furs, and he would sell them and repair them. He used to come from Appleton, Wisconsin to sell his furs at the the DesChamps shop which is where Regalo Luxury Gifts is now. While the business was based in Appleton, WI, it was called Myer’s Fur Post, traveling all over the U.P. selling their furs. As they transitioned out of furs, they became a clothing store. Originally, their store was located in the pocket park on River Street until the front of their building started falling off and forced them to move. The bar that is now part of the pocket park used to be the fur vault. They moved to their current location in 1971 and started adding clothing. Ellen started working in 1972 with her father until his passing in 2014 and Ellen took over.  

Many of the business owners that have been here the longest have seen Downtown Alpena through some of its hardest moments. “I remember when the mall came in and everyone was concerned about the mall coming in and the new businesses, but we survived. And now we see that the downtown has really come back and it’s the place to be now,” says Ellen Gould.  

While Downtown Alpena has grown into a popular location, that itself hasn’t come without struggles for the businesses. The way that we as a community have changed our shopping habits and our attention has been turned to a new era of technology, the retailers that we have are forced to reach much further. “The way that business has evolved, it used to be that you were in competition with the guy across the street and now you’re in competition with the whole world. That makes a huge difference in learning how to be competitive.” 

Downtown has thrived before and is thriving again. Our longest-lasting businesses are a testament to the tenacity it takes to survive in an ever-changing and growing environment. While there are still things to improve upon in Downtown Alpena, it has become a hotspot of culture, art, character, and growth in Northern Michigan. Gaining a different perspective on what downtown used to be can only benefit us as we move forward to plan its future, and we are so grateful to have so many business owners who have stayed in Downtown Alpena for so many years.  

A special thank you to Steve Wilson, Wayne Calkins, Jim Masters, and Ellen Gould for sharing the history of their businesses and their perspectives on the downtown with us! Without their contributions—and commitment to downtown—our downtown would look very different than it is today.  

Thank you to Alpena County George N. Fletcher Public Library Special Collections for all archival images.