Three Oaks Reconnected Its Main Street Just Before 4,000 Cyclists Rolled Through

Ashley Morgan settled on the name for her new bookstore after a line from a David Whyte poem kept surfacing in her head: "the big Midwestern skies over the farms surrounding Three Oaks." She opened Wind and Stars on July 4 inside Commune+Market on North Elm Street, taking over the space a fabric and craft studio, Handmade Studio, had just vacated when it moved to Sawyer in March. It's a small addition to a two-block downtown. This year, though, it didn't arrive alone.

Within the same twelve weeks, that same short stretch of streets got its only bridge back after years of delay, and then hosted the 53rd running of a bicycle tour that brings more outside visitors into the village in a single day than actually live there. None of this is three separate items for a newsletter. It's the same small village settling into a version of itself that looks a little different from the one residents navigated a year ago.

A Bridge Three Years in the Making

The Hickory Street bridge carries traffic over the Amtrak line that splits the village, and by 2022 it had a problem. Engineers from Wightman and Associates told the Village Council the box beams had been damaged by water and the bridge's load limits needed to come down for safety. Three Oaks teamed up with the City of Niles, the City of Watervliet, and the Village of Baroda to chase state bridge funding that year. Three Oaks was the only one of the four that got it.

The Village Council approved a $3.1 million engineering contract with Wightman in February 2025, with construction expected to start that spring. It didn't. An Amtrak easement requirement and a demolition plan the railroad wanted first pushed the timeline into the spring of 2026. Once crews finally got moving, they made up ground fast. By March 2026, the old bridge was nearly demolished and the project was running ahead of schedule. Beam setting wrapped in April, decking followed, and the bridge reopened to traffic in mid-July.

On September 3, the Village of Three Oaks and the Harbor Country Chamber of Commerce dedicated the rebuilt bridge in honor of John C. Kramer, a lifelong resident who walked the halls of Three Oaks schools from 1951 to 1963, served in the Navy through the Vietnam War, and spent 30 years building things around the village with his masonry partner, Butch Schwark. Village President Steve Graziano cut the ribbon on the newly paved surface. For a village that had spent the better part of three years watching this project move from safety concern to funding fight to construction delay, the dedication marked the point where the bridge stopped being a problem to track and went back to being just a bridge.

Where the Studio Used to Be

Wind and Stars sits inside Commune+Market at 105 N. Elm Street, sharing the building with Alan Ray's coffee shop. Morgan, an architect by training and a part-time Union Pier resident, had been a regular at Alan Ray's for years before the adjacent space opened up. She's planning fall programming that includes a children's story hour, author talks, and book clubs, along with collaborations with other small businesses in town.

It's a quiet kind of opening. No ribbon cutting, no council resolution. But it's the sort of addition that changes what a short walk down Elm Street actually offers, coffee and a bookstore under one roof instead of a coffee shop and an empty storefront.

The 53rd Apple Cider Century Takes a Different Road

Three Oaks Spokes Club has run the Apple Cider Century since 1974, and this year's edition rolled through the village on September 27 as the 53rd running. Club president Bryan Volstorf said riders had seven route options this year, from 15 to 100 miles, covering ground across Southwest Michigan and Northwest Indiana. One route changed for 2026: instead of tracking closer to the Lake Michigan shoreline through Red Arrow Highway and the New Buffalo area, cyclists rode from Lake Township Park to La Lumiere School instead.

The weekend follows a set rhythm that hasn't changed even as the route has:

• Saturday afternoon check-in, followed by a free ice cream social with live music at Dewey Cannon Park
• Sunday morning routes opening at 7 a.m., with an all-you-can-eat pancake breakfast from the Three Oaks Fire Department
• A spaghetti dinner waiting at the finish line

According to the event's own site, the ride draws as many as 4,000 participants each year. Three Oaks' estimated population in 2026 is just under 1,400. For one Sunday, the village hosts nearly three times the number of people who actually live there, all funneling back through the same two-block downtown that just got its bridge back.

Anyone who has ridden or watched this tour over the past several editions did so while Hickory Street's bridge was somewhere between deteriorating, funded, delayed, and torn down. This is the first year riders finished their loop crossing a bridge that's actually done.

What Changed Between the Ribbon and the Ride

Twenty-four days separated the bridge dedication from this year's Apple Cider Century, and Wind and Stars had been open for less than three months by the time riders passed its window. Taken on their own, a finished infrastructure project, a new bookstore, and an annual bike tour don't sound like they belong in the same story. Taken together, they mark a specific stretch of downtown Three Oaks working the way it's supposed to for the first time in a while: a reconnected Main Street, a filled storefront, and the village's biggest weekend of the year passing through both without a detour sign in sight.

Wind and Stars is starting its story hour and author series this fall, giving that same two blocks a calendar of its own for the first time since Handmade Studio left.

If watching Three Oaks come back together this season has you thinking about what it might mean for your own place in the village, Meghan Maddox can walk you through a free home valuation whenever you're ready to talk.