DAY HIKES
Chicago Riverwalk & Lunch at Washington Hall
December 1 & 3, 2026
Dec. 1 or 3
4-hours
$25.00
Difficulty rating
Miles
Approx 5+ miles
Terrain
Pavement and stairs
What to Expect
Join Trailbound Trips for an urban walk to enjoy Chicago’s natural spaces, art, culture, and Chistmas cheer. Our route takes us from the Ogilvie train station to Chicago’s Riverwalk to the Lake front, Cancer Survivor’s garden and onto the Bean. After the Bean we will sing a few Christmas Carols to the Chicago Christmas tree to put us in the holiday spirit. Lastly, we head to Washington Hall for lunch where one can choose from 9 different restaurants with one common eating area. After lunch, you are on your own to either head home or stay and enjoy the city. Browse the Christkindlmarket, or on Thursday, shop at the “One of a Kind” hand-crafted and speciality items at the Merchandise Market. Walks take place on Dec 1st and Dec. 3rd at 10:15am at the Ogilvie Train Station lobby. The entire route is approximately 5 miles. Cost of lunch not included. Our group times ends at lunch.
Washroom
Washroom in the train station
What to Bring
Water
Rainwear as needed
Sturdy walking shoes
Dress in layers for comfort
Emergency Medical Information form filled out (this is kept in your backpack, and only accessed in emergencies)
Lunch
We will stop at the Washington Food Hall for a wide variety of choices with their 9 different vendors under one roof. Under new management, this Hall is getting great reviews from Chicago’s Food Magazine.
Times
We meet by 10:20 am and begin our walk at 10:30. As a courtesy to all women, please arrive early, as we will begin promptly and not wait for latecomers. On the return trip, there is a Metra UP- NW train at 2:35, or you may choose to stay longer in the city.
Let’s Fully Savor the Outdoor Serenity
We ask you kindly to silence your phones and keep conversations positive.
Weather
We have fun in all kinds of weather, so we rarely postpone. If we do cancel a hike, you will receive an email before 8am the morning of the hike.
You Will Learn
We will learn about the history of the Riverwalk and some of the buildings along the walk.
Driving Directions
Meet at Ogilvie Transportation Center
500 West Madison Street
Chicago, IL 60661
We will meet on the ground floor, inside the lobby facing Madison Street at 10:20am. Meet near the Hudson Booksellers store.
(Those from the Northwest Suburbs can ride the train on the UP-NW 642 line, leaving Palatine at 9:12am)
Discussion Starter Question
The holiday season is truly upon us once again! What special activities or traditions do you like to purposely engage in during this time to ensure it’s filled with genuine joy and meaningful moments, rather than just a whirl of endless busyness?
Guides
Kari aka “Lucky Duck”
Quote of the day
"She is always a novelty; for she is never the Chicago you saw when you passed through the last time." - Mark Twain
Cancellations
If you desire to cancel your day hike, you can reschedule for a different hike within the season:
Please email hello@trailboundtrip.com, and state your name, and desired new hike day.
You will receive confirmation for this new day hike if there is room on the trip.
Refunds
Refunds are given when Trailbound Trips cancels a hike. Trailbound Trips will cancel and refund a hike for two reasons:
There needs to be a minimum of five people. You will be notified 24 hours in advance if this is the case.
The weather is dangerous, ie. lightning or a major storm. You will be notified before 8 a.m. on the day of the hike.