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Ashland might be a small dot on the map, but the neighborhoods here each carry their own flavor. The newer subdivisions—like those springing up near Liberty Lane—tend to cater to families craving modern floor plans, spacious garages, and sidewalks for the kids to run around on. You’ll see plenty of joggers and evening walkers, giving off that friendly, suburban feel. Move a bit farther from the center of town and you might stumble upon older homes with sprawling lots—perfect if you’ve been dreaming of a garden or want some extra distance from the neighbors.
In general, people who move to Ashland love the pace of life. You’ll run into all sorts—young professionals commuting to Columbia or Jefferson City, retirees seeking a quieter existence, and families who want their kids to grow up in a place where they can still ride bikes until dusk without worry. There’s a strong sense of looking out for one another, whether it’s stopping by a neighbor’s barbecue or chatting in the aisles of the local grocery store.
While it’s not brimming with big-box stores on every corner, Ashland offers the basics: a couple of grocery options, local gas stations, and small shops. Need more? You’re a quick drive to Columbia for big-name retailers or specialized services. And let’s talk about commutes: Highway 63 is your lifeline, connecting you north to Columbia or south to Jeff City in no time. There’s not really a bus system to speak of, so a car is essential. But hey, no crazy city traffic means you’ll spend less time on the road and more time enjoying life at home.
Ashland’s charm also lies in its rural surroundings. You don’t have to go far to find rolling farmland, winding country roads, and that unmistakable Midwest sunset lighting up the horizon. Nature buffs can easily escape to nearby conservation areas or fishing spots. When the kids get restless, a quick trip to Eagle Bluffs or Mark Twain National Forest (a bit further out) will scratch that outdoor itch.
So what can you expect when you plant roots here? Friendliness. Neighbors who actually say hello. A decent amount of elbow room. And a sense that, while the city is growing, it still holds tight to that small-town fabric. All in all, Ashland is a gem for those who want a break from the buzz but still appreciate having city life within arm’s reach.
Ashland is served by the Southern Boone County R-I School District, which has consistently earned respect for both academics and extracurriculars. Southern Boone High School is known for its Eagle pride—especially on the sports fields. Football Fridays can light up the whole town, and the basketball team often draws a crowd when they’re up against local rivals. Don’t be fooled into thinking it’s just about athletics, though. The school offers Advanced Placement courses and a range of clubs that keep students challenged and engaged.
You’ll find Southern Boone Middle School just a stone’s throw away, which helps create a nice transition for kids moving up through the grades. Parents often praise the teachers’ dedication and the sense of community around everything from band concerts to science fairs. Then there’s Southern Boone Elementary, where class sizes are manageable, and the staff puts in extra effort to make sure younger kids get that strong foundation in reading, math, and social skills.
Stats-wise, test scores in the district consistently hover around or above state averages, reflecting the community’s commitment to quality education. The district also values smaller class sizes, so your kids aren’t just another face in the crowd. Beyond the core academics, you’ll see a big push for STEM opportunities, arts programs, and even agricultural education—perfect for a region where farmland meets suburban living.
And yes, the sports teams garner plenty of local support. The Eagles have built a reputation not just in football and basketball, but also in softball, baseball, and track. Game nights become mini community gatherings, where you’ll likely see your neighbors, coworkers, and even your realtor cheering on the home team. It’s a vibe that reminds everyone of the town’s close-knit feel, where schools aren’t just institutions—they’re hubs of community life.
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While Ashland might not boast a gigantic shopping district, it’s got enough gems to keep life interesting. For everyday essentials, you’ve got local convenience stores and a small Moser’s grocery. If retail therapy calls, Columbia is just up the highway, offering big-box stores, malls, and plenty of boutiques. That said, people around here love to support local, so you’ll find a handful of family-run businesses that add character to the scene.
As for dining, Ashland Pizza & Pub is practically a local institution—there’s something satisfying about grabbing a slice and a cold drink after a long week. If you’re into barbecue, check out SoBoCo Smokehouse for a classic smoked-meat fix that’ll leave you licking your fingers. And if you want something a little more upscale, you can always hop in the car and be in Columbia’s bustling food scene in about 15 minutes.
For fitness and sports, you’ll see folks hitting up the local YMCA (in nearby Columbia or Jefferson City) or smaller community fitness centers. Some prefer running or biking on the country roads, which offer a scenic backdrop you just don’t get in bigger cities. There are also local youth leagues for everything from baseball to soccer, meaning the kiddos have plenty of options to burn off energy.
When you need a breath of fresh air or a weekend adventure, Ashland’s location is unbeatable. You can be hiking at Rock Bridge Memorial State Park or exploring Eagle Bluffs Conservation Area in no time. And if you’re craving a day trip, both Lake of the Ozarks and Mark Twain National Forest are within a reasonable drive, offering camping, boating, fishing—whatever gets you back in touch with nature.
Bottom line: life in Ashland may not be jam-packed with big-city attractions, but there’s plenty to keep your weekends full—whether you’re a homebody craving a good slice of pizza or an outdoor fanatic itching to hit the trails.
Ashland’s community spirit is the kind that wraps itself around you in the best possible way. People here love to celebrate—think local fairs, holiday parades, and small-scale festivals that might not make headlines but bring the whole town together. One of the staples is the Ashland Fall Festival, complete with crafts, food stalls, and a lineup of community performances. It’s the kind of event where you’ll recognize half the people you pass and probably meet a few new ones too.
The population last I checked sits around 5,000, give or take a bit. That relatively small number means you’re never far from a friendly face. It also means local businesses thrive on personal connections. You’ll see shop owners greet customers by name, and new places opening up with the support of neighbors who can’t wait to give them a try. Small-town living might be slower, but you’ll feel that intangible sense of “we’re all in this together.”
Don’t let the size fool you, though—Ashland’s on the rise. New housing developments keep sprouting up, more families are planting roots, and a growing number of commuters realize they can work in Columbia or Jeff City without sacrificing the perks of a laid-back hometown. Growth can be messy at times—hello, road construction and a sudden influx of moving trucks. But that messiness is also a sign of life. The city is evolving, and it’s got the potential to become an even tighter-knit hub of activity.
Through it all, one thing remains constant: Ashland’s sense of camaraderie. Whether it’s a high school sports game, a volunteer cleanup effort at the local park, or a spontaneous potluck in someone’s backyard, you’ll see the same faces popping up time and again. Everyone pitches in, everyone cares, and everybody’s welcome at the table. It’s raw, real, and doesn’t pretend to be some polished metropolis. If you’re into that vibe—a place where you can forge genuine relationships and watch your community grow—Ashland might just be calling your name. And if it is, Cheryl Maupin’s the perfect guide to help you find your own little piece of this hometown haven.
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The Milestone Group brokered by Real brings you that local boutique service you have come to know and love backed by a tech powered brokerage.
The Milestone Group has a continuous love for growth. Helping buyers and sellers grow in their knowledge of real estate and making educated financial decisions.
We are dedicated to helping our investors grow their real estate portfolios to financial success, being a small milestone in that journey.
We are a real estate group that continues to help each other grow personally, professionally and financially, so we can all flourish , and provide a real estate experience far above and beyond the average.
The Milestone Group is a team here to grow someone's dream, someone's vision, someone's desire to be and do more through real estate.
Cheryl is the founder of the Milestone Group and has been in the real estate industry for over 12 years. She started in real estate straight out of college and never turned back.
Outside of real estate she is a mom of two children, Ralston and Riley. Wife to Steven Maupin. And dog mom to the cutest little golden doodle, Alfie.
Her favorite hobby is riding and showing horses. She recently accomplished one of her personal milestones and bought her first show horse, Alison.
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