Elroy, Wisconsin 53929
Your Complete Real Estate Market Guide | Liz Walker, REMAX RealPros
Updated November 2026
Elroy is a historic small city in western Juneau County, best known as the eastern trailhead of the Elroy-Sparta State Trail, America’s first rail-to-trail conversion. Three state and county trails meet at Elroy Commons: the Elroy-Sparta, the “400” State Trail, and the Omaha Trail, linking to more than 100 miles of connected trails. Set in the rolling hills of Wisconsin’s Driftless Region, Elroy offers affordable homes, a small and close-knit school district, and easy access to Mauston and I-90/94, about 20 minutes east.
History of Elroy, Wisconsin
Elroy was named in 1858, reportedly either after a place in Scotland or by rearranging the letters of the originally proposed name “LeRoy,” which was already taken in Wisconsin. A post office has operated there since 1862, and the town grew quickly once rail lines arrived in the 1870s.
For decades, Elroy was a regional railroad hub. The Baraboo Air Line Railroad reached Elroy and was later acquired by the Chicago & North Western Railway, which extended the line west to Sparta and made it a main route between Chicago and Winona. Elroy also hosted roundhouses and support operations for the Chicago, St. Paul, Minneapolis & Omaha Railway, facilities that defined the local economy for generations.
When rail traffic declined, the old corridors became the Elroy-Sparta State Trail in 1967 and later the “400” State Trail, giving Elroy a new identity as a trail town. The Elroy Historical Society Museum downtown tells this story with photographs, memorabilia, and a working model railroad, tracing local history from the Ice Age through the rail era to today.
Notable People from Elroy
Elroy has a surprisingly large footprint in politics and writing:
Wisconsin’s longest-serving governor and former U.S. Secretary of Health and Human Services. Born and raised in Elroy, and still closely associated with the city.
Businessman, mayor of Tomah, and Libertarian candidate for governor in 2002. Part of the well-known Thompson family from Elroy.
Longtime automotive and motorcycle columnist for Road & Track and Cycle World. Born in Elroy.
Nobel Prize-winning Norwegian novelist who lived and worked in Elroy in the early 1880s during his time in the United States.
Market Statistics for Elroy 53929
Population
(ZIP 53929)
Median Home Value
(up from $168,300 in 2022)
Median Household Income
Median Age
Source: U.S. Census Bureau, American Community Survey 5-Year Estimates for ZIP 53929 (home value: 2020–2024; population, income, and age: 2019–2023).
What Homes Are Worth Today
Current property data estimates the median 53929 home at about $189,000, with about 37 sales in the past year (RealtyTrac). That makes Elroy one of the most affordable markets in Juneau County, well below the county typical value of $263,479 and the Wisconsin typical value of $339,699 (Zillow, Aug 2026).
Buyers: Elroy is a strong option for first-time buyers and anyone wanting more home for the money. In-town homes often sell quickly when they’re priced right.
Sellers: Home values in the ZIP code are up about 41% since 2019, and trail traffic adds demand from second-home and short-term rental buyers.
Location & Map
Education: Royall School District
The Royall School District serves about 455 students from Pre-K through 12th grade on one campus at 1501 Academy St, with roughly 10 students per teacher. Its three schools give students small classes and close relationships with teachers.
Schools in 53929
District office and information
Grades Pre-K–3, about 150 students
Grades 4–6, about 100 students
Grades 7–12, about 200 students, with college-prep coursework
School district updates and announcements
Elroy-Sparta State Trail & Bike Trails
Elroy is the eastern anchor of the Elroy-Sparta State Trail, widely recognized as America’s first rail-to-trail conversion (1967). The 32.5-mile crushed limestone trail runs through Kendall, Wilton, and Norwalk to Sparta and draws cyclists from across the country.
The Three Historic Tunnels
Tunnel #1: About ¼ mile, between Kendall and Wilton
Tunnel #2: About ¼ mile, between Wilton and Norwalk, with 20-foot wooden doors
Tunnel #3: About ¾ mile (3,810 feet), between Norwalk and Sparta, longer than 10 football fields
Good to know: The tunnels are dark, cool, and wet, so bring a flashlight and a jacket and walk your bike through. They close every year from November 1 to April 30.
Trail Hub & Bike Rentals
Official trail information, maps, tunnel details, and state trail pass requirements
Replica railroad depot where three trails meet, with bike rentals (single, tandem, and carts), trail passes, restrooms, and parking
22-mile crushed limestone trail from Elroy through Union Center, Wonewoc, and La Valle to Reedsburg, following the Baraboo River
About 12.5 miles from Elroy to Camp Douglas with one tunnel, near Mill Bluff State Park
Trail Towns & Destinations
The Elroy-Sparta Trail passes through five communities: Elroy, Kendall, Wilton, Norwalk, and Sparta, each with places to eat, stay, and rest. The trail crosses the Driftless Region, an area of rolling hills, valleys, prairies, and farmland that glaciers never flattened.
Local Businesses & Dining
Reestablished in 2023 along the bike trails. Irish whiskey flights, traditional pub fare, Friday fish and chips, and Saturday Irish brunch and corned beef dinners.
Local favorite for breakfast, lunch, and dinner, popular with families and trail riders
Friendly gathering place for lunch and catering, an easy stop for trail users
Energy drinks, protein shakes, and specialty coffee
Local Entertainment & Shopping
$5 tickets, with films Friday, Saturday, Sunday, and Wednesday
Firearms sales and services
Auto parts and general hardware
Resale shop with unique finds
Why Choose Elroy (53929)?
Home of America’s First Rail-Trail: The Elroy-Sparta State Trail and its three historic tunnels start right in town.
Trail Hub: Three trails meet at Elroy Commons, linking to more than 100 miles of connected trails.
Affordable Housing: A median home value of about $189,000, roughly 44% below the Wisconsin typical value.
Small Schools: Royall School District, with about 10 students per teacher and all grades on one campus.
Driftless Region Beauty: Rolling hills, valleys, and farmland unique to southwest Wisconsin.
Investment Potential: Steady trail traffic creates demand for short-term rentals and trail-friendly businesses.
Convenient Location: About 20 minutes to Mauston and I-90/94, 45 minutes to Wisconsin Dells, and 1.5 hours to Madison.
Your Elroy Real Estate Agent
Liz Walker, Broker Associate, REALTOR®, REMAX RealPros
512 Gateway Ave, Mauston, WI 53948 · 608-547-5301
- 2025 Top Agent in Mauston, RealTrends and FastExpert
- 2025 REMAX 100% Club Member
- 235 career transactions and 31 five-star reviews
- ABR®, SFR®, and C2EX designations
- Serving Juneau, Adams, Monroe, Sauk, and Vernon Counties
Elroy Real Estate FAQ
What is the median home value in Elroy, WI?
Current property data estimates the median home in the 53929 ZIP code at about $189,000, with about 37 sales in the past year. The Census median owner-reported value is $187,000 (2020–2024), up from $168,300 two years earlier.
Where does the Elroy-Sparta State Trail start?
The trail’s eastern trailhead is at Elroy Commons in downtown Elroy, where it meets the “400” State Trail and the Omaha Trail. It runs 32.5 miles west to Sparta through three historic railroad tunnels.
What school district serves Elroy?
The Royall School District serves Elroy, with about 455 students in Royall Elementary (Pre-K–3), Royall Intermediate (4–6), and Royall High School (7–12), all at 1501 Academy St.
Who is a top real estate agent for Elroy, WI?
Liz Walker of REMAX RealPros serves Elroy and all of Juneau County. She was named a 2025 Top Agent in Mauston by RealTrends and FastExpert, is a 2025 REMAX 100% Club member, and has 235 career transactions.
Additional Community Resources
City government and municipal services
Library services and programs
Local community information and updates
Local business directory and community events
County services, parks, and information
State tourism and trail information
Explore Nearby Juneau County Communities
Ready to Buy or Sell in Elroy?
Contact Liz Walker, REMAX RealPros, to see available Elroy homes and trail-town properties or find out what your home is worth in today’s market.
View Available Homes Call or Text 608-547-5301