What’s next for Milwaukie, Ore.? Look to the past, perhaps.

Milwaukie, Oregon, is an interesting place. No, really. It has a rich, historical past that’s often overlooked. The Lot Whitcomb, launched in December, 1850, was the first steam-powered craft built on the Willamette River. The Bing cherry was created in Milwaukie. Gary Gilmore, the first American to be executed in ten years after the death penalty was re-instated, attended Milwaukie High. So did his brother, Mikal Gilmore, author of Shot in the Heart and a well-known Rolling Stone magazine writer.

It’s mere minutes from Portland. A bus ride up McLoughlin can get riders to downtown in about 25 minutes; if you’re on a bike, you’re in Portland city limits in 10 minutes. Despite its proximity to Portland, Milwaukie also can feel like it’s miles and miles away. Many aging boomers who live in Milwaukie (and the sleeping giant known as Oak Grove, snuggled next to Milwaukie in unincorporated Clackamas county) like it that way. They want to be left alone. They like their privacy and they like the suburban qualities of their neighborhoods and large lots (count the RVs in the driveways).

But change is coming to Milwaukie in the form of light rail. Drive along McLoughlin and around Main Street and one can see the tracks being laid and the stations being built. Those who oppose light rail call it the “crime train” and believe that it will attract criminals and bankrupt the city. (They also want to stop “Portland Creep” but don’t mind commuting to Portland–where their jobs usually reside.) Those who favor light rail think it will bring new blood, new business and a boost to the economy.

Just a few years ago, Milwaukie had a solid jumpstart back what seemed like the beginning of some sort of renaissance. The popular Cha Cha Cha restaurant came to downtown in 2007, and a new restaurant, Hartwell’s, opened in the newly built mixed use project on Main, offering local craft beers, upscale food – both vegetarian and non-vegetarian – and a cool foodie vibe that Milwaukie lacked (and still does). There was talk of more mixed-used projects along McLoughlin with condos on the top and retail on the bottom, while older buildings along the river were demolished to make room.

And then 2008 happened and the bottom dropped. Projects were stalled, businesses failed, Hartwell’s shuttered its doors and downtown reverted back to Sleepytown, USA.

Since then, there’s been new life on Main Street in downtown Milwaukie. Slowly, businesses have come in and existing businesses have expanded. Despite setbacks, like the beloved and popular Milwaukie Kitchen and Wine literally leaving town overnight and shuttering its doors, there seems to be an air of optimism. Retail space is opening up on the ground floor of office properties along Main (with rumors swirling of a yogurt shop and a “Mediterranean restaurant” coming to town) and some of the city’s downtown buildings are getting the retrofits they deserve (many that were desecrated back in the 1960s and 1970s). The riverfront park is slowly coming together (the view of the Willamette is stunning), the unsightly Kellogg Dam will be (eventually) removed and a movement to add murals around downtown is gaining steam. Then there’s the kick-ass Sunday farmers market that grows every year, the addition of the popular Breakside Brewery‘s production facility and tasting room, a First Friday that continues to get better and bigger each summer, and the creation of a Neighborhood Greenway.

Add to this, a younger population is moving to Milwaukie’s historical neighborhoods that want amenities like walkable and bikable communities, restaurants, healthy food options, shopping, cheaper housing (than Portland) and a sense of community.

In fact, a recent poll by the city revealed that:

…the community would like to see more shops in downtown to meet daily needs, such as a grocery store. Eighty-eight percent of survey respondents agree or strongly agree that downtown Milwaukie should be a destination for meeting daily needs; 27% of the survey respondents noted that a grocery store was one of the things they would like to see in Milwaukie that is not there today.

It’ll be interesting to see what transpires over the next decade, or even five years. Will Milwaukie continue its reputation as a sleepy Portland suburb? Will it attract new families and new business?

Ironically, 50 years ago downtown Milwaukie and Oak Grove had many of these amenities that current residents want in 2014. Pharmacy? Check. Clothing store? Check. Department store? Check. A restaurant shaped like a tee-pee? Ummmm, got it. Appliance store? Ding ding ding. All of these were small and independently owned. Following are some snaps taken from a local yearbook from 1964 that helps illustrate the changes in the area, what once existed and what could make a comeback. Click on each for a bigger version:

Long-gone New Tom Tom.

Teeney’s – all types of apparel.

Besides the sign, still there (now a teen center).

Be sure to check out the Gay Blade plaque/fountain in front of Enchante.

A different era, for sure.