Early on a September Saturday, the water in Coffee Creek Watershed Preserve turns busy in a way most of the year it isn't. Trout and salmon move upstream through the shallows along the Long Loop, visible from the boardwalk if you slow down and look. A few miles away, cyclists are already rolling out from the Prairie Duneland trailhead on South 15th Street, some heading west toward Hobart, others taking a shorter route into downtown. At Thomas Centennial Park, vendors are setting up folding tables for another Saturday of the European Market, in the shadow of the park's historic bandstand.
What most of those riders still don't know is that a year ago this month, the town cut the ribbon on a route that finally lets you connect several of those threads without backtracking through the same half-mile of road twice. It is the kind of infrastructure that never gets announced twice, so unless you happened to be at Dogwood Park last September, there is a decent chance you are still riding the old way.
What Actually Opened Last September
The Westchester-Liberty Trail has been under construction since 2008, arriving in three separate phases that most residents only ever experienced through whichever segment sat nearest their own street. Phase 1 was finished in 2008. Phase 2, which linked Dogwood Park to Chesterton High School and the Boys and Girls Club, followed in 2017. Phase 3, a half-mile extension along County Road 1100N, wrapped up in 2025, and the town marked it with a ribbon-cutting that September, closing out a project that took seventeen years to build in three pieces.
| Phase | Completed | What it added |
|---|---|---|
| Phase 1 | 2008 | First segment built from Dogwood Park |
| Phase 2 | 2017 | Linked Dogwood Park to Chesterton High School and the Boys and Girls Club |
| Phase 3 | 2025 | Extended the trail a half mile further along CR 1100N, ribbon-cut that September |
At the ceremony, Town Council member Jim Ton laid out what the finished segment actually makes possible: a pedestrian or cyclist can now travel from the Prairie Duneland trailhead on South 15th Street to 23rd Street, south into Dogwood Park, out to 1100N, and east to County Road 100E, all on dedicated trail rather than roadside shoulder. Park Board President Paul Shinn described the same stretch as something that connects local parks, schools, and neighborhoods, language that reads like boilerplate until you consider who actually uses 1100N every week: the students, parents, and visitors who drive it to reach the Chesterton High School campus for games and events.
The Loop, As Town Officials Describe It
Combine that new segment with the Prairie Duneland Trail and you get what local officials have started calling the Chesterton Loop. From the 15th Street trailhead, the route runs south to 23rd Street, into Dogwood Park, east along 1100N to 100E, then loops back north on South Calumet Road into downtown at Broadway, before returning to the 15th Street trailhead. If you want to keep going from there, the Prairie Duneland Trail continues west through Portage to its terminus in Hobart.
It's worth being precise about scale here, since the numbers get conflated easily. The full Prairie Duneland Trail runs 10.3 miles between Hobart and Chesterton. Only about three of those miles, from 15th Street to State Road 149, actually sit inside Chesterton town limits. The Westchester-Liberty segment is what turns that three-mile stretch from a there-and-back ride into an actual loop through Dogwood Park and back downtown, and the Calumet Road return leg happens to pass Lucrezia Café at 428 South Calumet, a reasonable place to end a Saturday ride.
What's Still Just a Plan
The temptation with a project like this is to round up, so it's worth being just as precise about what has not happened yet. The Westchester-Liberty Trail's stated long-term purpose is to eventually link the Prairie Duneland Trail to the Dunes Kankakee Trail, the corridor that is meant to someday run the length of Porter County from Indiana Dunes National and State Parks down to the Kankakee River. That link does not exist yet. At the same ribbon-cutting, Ton described the next segment, from 100E south to the railroad, as something that may eventually become a portion of the proposed Dunes Kankakee Trail, in his words, in theory at this time. That is town-council language for: this is the plan, not the current reality.
The Dunes Kankakee Trail itself has a long way to go on its own. A 2016 trail survey put its built length at just 1.8 miles, running from the state park's entrance gates to the Indiana Dunes Visitor Center. Nothing in the record suggests that stretch has been meaningfully extended since. So the honest version of this story is that Chesterton finished a genuinely useful local loop last fall, not a new bike route to the dunes.
What's Moving in the Creek Right Now
Coffee Creek Watershed Preserve, at 2401 Village Point, is 157 acres and has been in place since 1998, with five miles of trail through restored prairie, wetland, and woods. The Long Loop, a 2.9-mile stretch of pavers, boardwalk, and wood chips, is the section worth timing your visit around this time of year, because the creek itself becomes the attraction. Salmon and trout move through it during spring and fall spawning, and the boardwalk sections put you close enough to watch without disturbing them. White-tailed deer and red foxes turn up along the quieter stretches, particularly early in the morning before the trail gets busy.
It's worth separating this preserve from Coffee Creek Park, a smaller, closer-to-downtown green space at 246 East Morgan Avenue with its own short boardwalk trail. Locals sometimes use the two names interchangeably, but they're different places with different reasons to visit. The park is a five-minute stop next to the historic business district. The preserve is the destination for the fall spawning run and the longer walk. Both are dog-friendly on leash, and the preserve charges no admission, which keeps it in regular rotation for people who walk the same loop weekly rather than treating it as a special trip.
The Market's Last Stretch
The European Market runs every Saturday from May through October, 8 a.m. to 2 p.m., at Broadway and Third Street next to Thomas Centennial Park, home to the town's historic bandstand and a repurposed rail boxcar and caboose the town installed in 2018. It draws vendors from Indiana, Michigan, and Illinois selling everything from artisan bread to handcrafted jewelry, with live music from Duneland-area musicians most weeks. It's dog-friendly on leash, which matters if your Saturday already started at a dog-friendly trailhead a few miles away.
The market's season has a built-in finale. Its last Saturday each year turns into Pumpkin Palooza, a Halloween-themed version of the same market with trick-or-treating at vendor booths, pumpkin painting, and costume contests for kids and dogs. It's the kind of local tradition that never makes an out-of-town visitor's itinerary but anchors the calendar for people who actually live here, the same way the creek's fall run does.
One Saturday, Three Stops
With the Chesterton Loop now a real, ridable route rather than a plan on a council agenda, a resident who wants to use all three pieces in one outing finally has an actual path to follow.
- Start at Coffee Creek Watershed Preserve on Village Point early, while the light is low and the creek traffic is easiest to spot from the Long Loop's boardwalk sections.
- Drive or ride the short distance to the Prairie Duneland trailhead on South 15th Street, then pick up the loop south to 23rd Street and through Dogwood Park, out to 1100N and back north on South Calumet Road.
- Finish at Broadway and Third for the European Market, timed for late morning when the vendor tables and live music are both in full swing, with Lucrezia a short detour away if the ride runs long.
Why the Small Piece Matters More Than It Looks
It's easy to treat a half-mile trail extension as a rounding error, especially next to a 10.3-mile rail-trail that already gets treated as the town's signature outdoor asset. But the Westchester-Liberty Trail was never trying to compete with Prairie Duneland on distance. Its value was always in what it connects, not how far it runs on its own, and seventeen years after the first phase broke ground, it finally does what it was designed to do: turn a there-and-back ride into a loop through the neighborhoods that actually use 1100N every week for school games, Boys and Girls Club programs, and trips downtown.
This is the texture that makes a place feel lived-in rather than just visited, the sort of local rhythm that shows up in daily routines long before it shows up in any market report. It's also exactly the kind of on-the-ground detail our team at Matt Evans tracks closely, because understanding how a town actually functions on a Saturday morning is part of understanding its value the rest of the week. If you're weighing a move in or around Chesterton, or just curious what your current home is worth in a market that keeps adding reasons to stay, get your free home valuation and let's talk about what's changing here.
