Discover Downtown Westbrook is excited to host a series of Jane’s Walks throughout Downtown Westbrook on Saturday, May 3rd!
Jane’s Walks are citizen led informational walks that have become popular nationwide. These walks are held in memory of Jane Jacobs, an activist who fought against the urban development of Central Park. You will have the chance to join a variety of Jane’s Walks in Westbrook with topics including the history of the Presumpscot river, future plans for the downtown area, and the development of walking trails in Westbrook.

Jane’s Walks are being organized by Discover Downtown Westbrook. Thank you to our volunteer leaders!
Learn more about Jane’s Walks in Maine HERE.
2023 featured 4 walks from community leaders. We are excited to offer more walks this year!
The walks will take place throughout downtown on Saturday, May 4th. Each walk averages about an hour but will start at different times and locations. Schedule to be released soon. 🥾💓
2025 Schedule at a glance:
A day packed full of education, connection, and celebration of Westbrook!
Imagine Places Here: The Parking Craters of Downtown Westbrook at 8:00 AM
Exploring engineering, stormwater design and trails in our downtown at 10:00 AM
A Walk Down History Lane at 11:00 AM
Downtown Thrift Walk at 12:00PM
Little Free Library Ride at 1:00 PM
A Market Hop at the Westbrook World Markets! at 2:00 PM
Saccarappa Lands and Waters: The Past and New Futures of an Ancient Site at 4:00 PM
2025 descriptions below.
2025 Highlights
Scroll for times, meeting locations, and themes for our 2025 walks. No registration required but please share and RSVP on Facebook!
Imagine Places Here: The Parking Craters of Downtown Westbrook
by Cary Tyson
Time: 8:00 AM
Meeting Location: 850 Main Street
Distance: 1 hour, 1 mile
Parking is all the talk of downtown Westbrook. Is it a parking problem or a walking problem? Walk the parking craters of downtown Westbrook with an eye for the highest & best use.
Engineering, stormwater design and trails in our downtown
by Rhonda Forrester
Time: 10:00 AM
Meeting Location: Riverbank Park Gazebo
Distance: 1 hour, 1.5 mile
Curious about the engineering infrastructure working behind the scenes in our downtown? What do we, and should we, consider when connecting our neighborhoods? What’s so important about stormwater, anyway?
Join us for a walking conversation about Civil Engineering and Urban Planning. We will go over the planning and design necessary to create urban landscapes, and also talk a little about Westbrook history and the trails you can access right from downtown. The meandering walk of just under one mile will start at the gazebo in Riverbank Park and our conversation will take us to the Cornelia Warren football field, and then along the river trail to the boardwalk.
A Walk Down History Lane
by Mike Sanphy
Time: 11:00 AM
Meeting Location: 389 Main Street, Westbrook
Distance: 1 hour, 1 mile
Beginning at The Elm’s Inn on River Road/Cumberland Street, we’ll take you back in time to the mid to late 1800’s when our Mills were operating at full steam ahead, homes were being built for the owners, residents and workers.
We’ll continue along the river to the Warren Block, Nathan Harris House (circa 1828) and end down by the river through the Warren Recreation Field (with a beautiful view of The Elms from the river side of the home) to learn about the infamous “Boy & his Dog” Statue.
Wear comfortable clothing, comfortable walking shoes and maybe some water if it’s a hot morning. Be prepared in the event of poor weather as well (umbrella’s, warmer clothing).
Downtown Thrift Walk
by Abby Wilson
Time: 12:00 PM
Meeting Location: Dana Warp Mill Lobby (Main Entrance / Door 7), 90 Bridge Street
Distance: 1.5 hours, 1 mile
Bring a bag and your wallet for this Jane’s Walk! Abby Wilson, Discover Downtown Westbrook Event & Volunteer Coordinator and Westbrook resident will be taking you on a tour of Westbrook’s thrift stores.
We will meet in the lobby of the Dana Warp Mill and begin by visiting one or two studios that sell used goods. Northstar Vintage has a great collection of secondhand clothes and will be open and ready to explore! Last but definitely not least is Bloom Consignment and Resale on Main Street where you can browse the inventory for a new spring look or hit up the sale rack for a great deal.
Little Free Library “Jane’s Ride”
by John Brooking
Time: 1:00 PM
Meeting Location: Westbrook Common, Westbrook
Distance: 1.5 hours
A leisurely-paced 90 minute bicycle ride with stops at a half dozen-plus of Westbrook’s “little free libraries”. Bring a book, leave a book (or several)! There’s even a Free Little Art Gallery art exchange. Enjoy interesting literary conversation along the way, and an optional post-ride gathering at one of our Bicycle Benefits businesses. Helmets encouraged.
A Market Hop at the Westbrook World Markets!
by Amy Grommes Pulaski
Time: 2:00 PM
Meeting Location: 506 Main Street
Distance: 1.5 hours, 1 mile
Join us to visit our Westbrook World Markets! This program is an initiative of Discover Downtown Westbrook that features five world markets representing delicious food, delicacies, supplies and other wares from around the world. We will be visiting three of the markets on foot: La Fontaine African Market and walking to Grace African and Caribbean Food Mart and Medeo European Food and Deli.
We will park near the intersection of Main Street and Rochester Street in Westbrook, and meet on the front steps of 506 Main Street. From here we will walk the 1/2 mile along Main Street to La Fontaine African Market located at 406 Main Street. We will then return along the same route to visit Grace African and Caribbean Market and Medeo European Food & Deli, located at 529 and 529A Main Street. At each location we will meet the owner, peruse the products and fashion and sample the delicacies.
You are encouraged to visit the other two Sindibad Halal Arabic Market and the African Supermarket on Brown Street, either with us by car, or on your own. Information about all five markets can be found on our website.
Saccarappa Lands and Waters: The Past and New Futures of an Ancient Site
by Michael Shaughnessy
Time: 4:00 PM
Meeting Location: Conant Trail, 105 Conant Street (next to Ernie’s Cycle Shop
Distance: 1.5 hour, 1 mile
Beginning at the Polin Memorial where we will speak to the rivers indigenous and its industrial past, we will walk down along the river into Downtown Westbrook to Saccarappa Park. While looking down and across the Western Falls of Saccarappa we will talk about the rivers and falls; historic importance, restoration efforts and successes, and the sites future . Along the way we will discuss development plans that will include housing, commercial space, and public spaces that include the extension of the Boardwalk into a path that would connect upriver to the Conant Trails. From Saccarappa we will walk up past the Dana Warp Mill were we can visit a secluded section of the Eastern Falls. There remnants of the industrial past are clearly seen as well as relics of a more geologic nature.
This is largely a mile hike. Bikes can be ridden or walked along the route. The terrain is a combination of nature path and sidewalk along city streets. It is uneven and may even be a bit mucky. It is advised to wear sturdy shoes or boots.
