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Check out this slideshow of our fabulous trip to Yellowstone, then sign up to join us on one of our weeklong trips!
Carol Ruhter

The Trailhead

From Carol Ruhter, Trailbound Trip’s founder and guide.

"When life feels too big to handle, go outside. Everything looks smaller when you’re standing under the sky." ~L.R. Knost

Register for these Fabulous Adventures

  • Wild Woman Tri~ June 12, 2019 Our 10th Annual Tri...A non-intimidating sprint-triathlon with friends
  • Fall Day Trips ~ April 16 - June 1, 2019 Walk on the Wild Side this spring! Rejuvenate your spirit and body with exercise, fresh air, sunshine, wildflowers, friends, and discovery. 1 Free Spring Hike - 1st-Time Trailbound Hikers Only
  • Arizona ~ Oct. 19-25 or Oct. 26-Nov. 1, 2019 Sedona and the Grand Canyon beckon... Oct 19-25 is full.

Adventures in the Making

  • Also coming in 2019!
    Autumn: Day Trips in Northern Illinois
  • Coming in 2020!
    Winter: Day Trips in Northern Illinois
    Discover Yellowstone in Winter (WY)
    Spring: Day Trips in Northern Illinois
    Door County Getaway (WI)
    Bryce & Zion (UT)
    Summer:11th Annual Wild Women Triathlon
    Washington State’s Wonders
    Autumn: Day Trips in Northern Illinois
    Kentucky’s Red River Gorge
    New York’s Finger Lakes
    Great River Getaway (WI & IA)

    Interested? Email and ask to be on our "1st dibs" list. No cost/obligation.

Get on the Wait List for these popular trips

  • White Pines Getaway ~ May 14-16 or May 17-19, 2019 Hike through towering pines...across babbling brooks...under the stars
  • Glacier National Park(MT) ~ July 13-20, 2019 -or- July 20-27, 2019 Discover stunning hikes, glacier-studded mountain peaks, wildlife galore, dips in glacial lakes, vibrant wildflowers, towering waterfalls, warm camaraderie, lifelong memories, and your own adventurous spirit!

  • Shenandoah ~ June 1-7 & June 8-14, 2019 For one amazing week, treat your spirit and body to a tranquil wilderness haven and outdoor adventure.
  • Apostle Islands ~ Aug. 3-7, 2019 or Aug. 7-11, 2019 The Apostle Islands offer an island retreat right in the Midwest! This archipelago of 22 islands is nestled in Lake Superior, off Wisconsin’s northern coast.
  • Acadia Nat’l Park (Maine) ~ Sept. 14-20 or Sept. 21-27, 2019 Watch the sunrise. Smell sea air. Listen to waves. Taste succulent lobster. Feel gentle ocean breezes.....
  • Explore Sheboygan Shoreline Getaway (WI) ~ Sept. 27-29 and Sept. 30-Oct. 2, 2019 Hike on pristine Lake Michigan beaches, cross rolling dune boardwalks, and along scenic lakes tucked in Wisconsin forests... Trek an autumn fantasyland of glacial kettles and moraines, hardwood forests and towering pines, tallgrass prairies and fall wildflowers...Explore ancient Native American effigies... Discover why some call Sheboygan the Malibu of the Midwest for kayaking, paddleboarding, and surfing...Relax in a 5-star resort.

Meet Our Trailbound Guide

Jill May
Jill May (aka "Chippermunk") leads Trailbound day hikes and getaways. Jill’s love of the outdoors began as a young child in the Girl Scouts. She’s an avid camper and hiker, and calls the woods her "happy place." A few of her favorite happy places include Southwest Colorado, Michigan’s Upper Peninsula, and the Great Smoky Mountains of East Tennessee. She also enjoys biking, kayaking, swimming and spending time with her family. As an Integrative Nutrition Health Coach, Jill works with kids who struggle with emotional and mental health issues and physical challenges. Jill lives in Palatine, IL, with her outdoor-loving husband and two sons.

Welcome to Trailbound Trips...

Our outdoor adventures delight, inspire, encourage, and strengthen women.

Join us for fun hiking and bicycling day trips in Northern Illinois’ wild places. Bike under canopies of autumn color and along rippling streams … hike through forests dappled with spring wildflowers or in tall grass prairies … discover coyote dens and follow deer paths … walk through pristine winter wonderlands.

Explore and enjoy the Midwest’s most beautiful gems. Dogsled through Lake Superior’s Northwoods … kayak gentle streams under covered bridges … hike behind waterfalls and through canyons … horseback ride and bike through woodlands and meadows … savor vistas and sunsets from 500-foot bluffs. (Trails by day — lodges by night.)

Follow your heart on weeklong dream trips to destinations like Acadia, Maine, nestled by the Atlantic ocean … Utah’s gorgeous red rock canyon-lands … Oregon’s coastline, cascades, and Crater Lake… Waterfall tours through Carolina’s Blue Ridge wilderness … Snow-capped mountain wildernesses packed with wildlife and beauty. (Trails by day; lodges by night).


  • Breathtaking beauty, unforgettable trails, and true outdoor adventure.
  • Your own adventurous spirit, renewed confidence, and exhilaration.
  • Tranquility: time to walk in silence, savor beauty, play outdoors again.
  • Friends who share your love of nature and the outdoors.
  • New ways to view nature and yourself through nature-based discussions. We also offer trips with a Christian focus, which are noted accordingly.

Enjoy this all with the friendliness, knowledge, and encouraging can-do attitudes of your experienced guides.

Join us! Explore. Dream. Discover.

Trailbound’s 2019 Schedule


  • Day trips in Northern Illinois:: Jan 2 - Feb 23. Guides: Scout, Wander Woman, Spirit, Zephyr & Chippermunk.
  • Northwoods Dog Sled Adventure (MI): Wed-Sun, Feb 22-26; Guides: Scout & LL Lucy


  • Day trips in Northern Illinois: Apr 16 - Jun 1. Guides: Scout, Wander Woman, Spirit, Zephyr & Chippermunk.
  • White Pines Getaway: May 14-16 & May 17-19. Guides: Scout and David R


  • Wild Woman Tri: Wed, June 12
  • Shenandoah National Park (VA): June 1-7 & June 8-14. Guides: Scout, Rebel & Wander Woman
  • Glacier National Park (MT): July 13-20 & July 20-27. Guides: Scout, Wander Woman & David R.
  • Apostle Islands (WI): Aug 3-7 & Aug 7-11. Guides: Scout & Randonee


  • Day trips in Northern Illinois: Sept 3 - Oct 26. Guides: Scout, Wander Woman, Spirit, Zephyr & Chippermunk.
  • Acadia National Park (Maine): Sept 14-20 & Sept 21-27. Guides: Rebel, Running Water, and Wander Woman
  • Sheboygan Getaway (WI): Sept 27-29 & Sept 30-Oct 2. Guides: Scout and River Rat
  • Sedona & Grand Canyon (AZ): Oct 19-25 & Oct 26-Nov 1. Guides: Rebel, LL Lucy and Wander Woman

~ Like us on Facebook ~

Be sure to like us, where you can check out the fun and the beautiful places we visit! You’ll love the great nature videos, quotes, and photos that Nancy posts...along with Trailbound’s activity updates and trip photos. To be sure you’re getting our page updates, be sure to "like," comment, and/or share our posts. And if you see yourself in one of our photos, go ahead and "tag" yourself so your friends can see what a great time you’re having with us! Because Facebook only sends our posts to about 20% of our list, the more you participate, the better the chance of Facebook sending you our updates. And of course, you can always visit our Facebook page directly at any time to see what’s happening. See you on Facebook!