
Discover Downtown Westbrook is excited to host its fourth annual Jane’s Walk Day on Saturday, May 2nd, 2026!
Jane’s Walk is a global festival of free, volunteer-led walking conversations inspired by community activist Jane Jacobs, who famously fought against the urban development of Central Park in New York City. Jane’s Walks are organized by Discover Downtown Westbrook and led by our volunteer leaders – a day packed full of education, connection, and celebration of Westbrook!
Learn more about Jane’s Walks in Maine HERE.
2026 Schedule
We’re excited to welcome new walks and walk leaders this year! Walk topics this year include an exploration of Westbrook’s history, stories of the Presumpscot River, a walking tour of our new downtown murals, an exploration of how Westbrook rolls, and more.
Scroll for times, meeting locations, and themes for our 2026 walks!

From Books to Bricks: Walking Westbrook’s Downtown
By: Chance Gagne
Time: 10:00 AM
Meeting Location: 800 Main Street
Duration: 1 Hour
Accessibility: There are some bus routes nearby. We will be following a lot of sidewalks and Dana Warp Mill has an accessible entrance along the side if needed.
This conversational walk moves from Walker Memorial Library through Westbrook Common, across the Presumpscot River, and into the Dana Warp Mill area. Along the way, we’ll explore how public spaces, civic institutions, and industrial sites have shaped everyday life in Westbrook and how people use (or don’t use) these spaces today. Expect observation, discussion, and shared stories rather than a formal tour. Please wear comfortable shoes and prepare in case it rains!

A Walk Past History
By: Mark Swett
Time: 10:00 AM
Meeting Location: 489 Main Street
Duration: 90 Minutes
Accessibility: Will be walking along sidewalks, over the bridge and up a slight hill. Handicapped entrance TBD at The Elms
Starting at the top of the historic Warren Rec Fields (behind BreaLu Restaurant ), overlooking the Presumpscot River, S. D. Warren Mill and one of our most historic homes, now called, “The Elms”, we’ll walk down Main Street towards the Warren Block; stop in to The Nathan Harris House now owned by the Westbrook Historical Society and view the beautiful 1830 hand painted murals – and end with a tour of The Elms by the owner, Greg Mitchell.

Maine’s Lost River Found: An Urban Adventure with the Presumpscot
By: Katharine Atwood
Time: 1:00 PM
Meeting Location: Lincoln Street Ice Rink, 58 Lincoln St
Duration: 90 Minutes
Accessibility: The walk is recommended for people who feel able to navigate some areas of rougher terrain. One part will take us down a narrow trail, so the entire walk is likely not wheelchair accessible. Please contact [email protected] for an accessible walk option. The lot is also accessible by a short walk from the transit-accessible Westbrook Downtown.
Join us on the banks of the Presumpscot River for this urban adventure to discover once-hidden waterfalls and stories of a lost river rediscovered. This river once held 13 named falls and many rapids, of those only three today can be found. Two of which were reborn due to recent dam removals, one of which we will get to experience up close on this walk. The Presumpscot is a river rich with secrets and history, including tales of treaties, a submerged farmhouse, lost apple orchards, powder mill explosions, buried coins, and much more. On this walk, we will also learn about the current work underway to rewild the river, the upcoming fish migration, and efforts to free the river once and for all. The river stretches 27 miles from Sebago to the Sea; come meet us along this incredible section. Our walk will be less than a mile total and take us up close to the rocky edges of the waterfalls.

Just ROLL With It: What A City’s Infrastructure Says About How it Values Young Families and Older Adults
By: Jill Johanning
Time: 1:30 PM
Meeting Location: 900 Main St
Duration: Less than 60 min
Accessibility: The intent of this walk is to be inclusive for all mobility devices. There will be sections of uneven/cracked sidewalks, sidewalks with cross slope, and curb ramps with steeper slopes. There are 3 Metro bus routes that have stops at or near the starting location of the walk, and a large parking garage.
Walkers are encouraged to bring their families with strollers/rollators/wagons/balance bikes to follow a route from the bus stop to the library to experience the opportunities and challenges along the way for residents and visitors who roll around downtown Westbrook. Conversation along the stroll will share the minimum requirements under laws like the Americans with Disabilities Act (ADA), Maine building codes, to Age Friendly programs, lessons learned and best practices to make main streets more welcoming for families with young children and older adults. Do downtowns work families who cannot or choose not to drive, for nursing mothers, families who need access to restrooms, changing station/tables, families who need a place to rest, a place to get cool or stay warm, places to socialize and connect with neighbors, are the sidewalks maintained during the winter to the same level as the streets, secure bike racks, pedestrian level lighting to feel safe, and is it fun? Are communities and businesses sharing the message of what is available for families on main streets to know if it will work for them when they visit? Are municipalities providing funding opportunities and incentives to encourage better access for pedestrians? The route will review existing conditions and alterations of sidewalks, business entrances, public spaces, and temporary events that impact our main streets to make sure that families of all ages are engaged in our communities and thriving downtowns.

Discover Westbrook’s Mural Trail
By: Savanna Bowen
Time: 1:30 PM
Meeting Location: 869 Main St
Duration: Less than 60 min
Accessibility: The walk does not cover a long distance (2/3 mile round trip), however, it does require standing and strolling.
Join us to discover the new and existing murals installed throughout downtown Westbrook, which highlight local creativity, enhance the visual landscape, and strengthen our community connection through art. The walk begins in Vallee Square where last summer community members gathered together to Paint the Street to celebrate our musical history and highlight our popular Vallee Square summer concert series. Next the tour will visit the legendary mural installed by Ryan Adams on the riverside of the Sindibad Market featuring two of Westbrook’s local legends- Pat Gallent Charette and Zoe Saoule. The walk will then weave through the downtown and highlight several murals contributed by emerging artists as part of our 4×4 Mural Project. The tour ends with the iconic Westbrook Mural, located in the Sculpture Garden along Main Street. During this walk, you will be led by Discover Downtown Westbrook’s Art and Culture Representative, and also key and contributing artists along the way.
The Westbrook 4×4 Mural Project is a partnership between Discover Downtown Westbrook and the University of Southern Maine, funded by the Warren Memorial Foundation. This project features a series of 4-foot by 4-foot murals created by students, local artists, and professional creatives hung throughout the downtown. At each Mural location, we will stop and discuss the mural, who painted it, its contents, its part of a 4×4 Mural Project, and what it has brought to our community of Westbrook.



