Portland, OR to Milwaukee, WI – Home of Harley-Davidson
[16 Days/15 Nights – July 31 – August 15, 2021]

Love the Harley-Davidson lifestyle? Ride to Live and Live to Ride? Start with us in Portland, Oregon, and ride with us to Milwaukee, Wisconsin. This registration option starts as our others do, at our West Coast Start Party in Portland. You’ll ride all the way to Milwaukee, most of the way across our great nation visiting historic sites, riding cool roads, and seeing the best of what this part of the United States has to offer. We’ll be riding secondary roads and avoiding highways as much as possible. Most days will be ~250 miles and there will be 2-night stops at Yellowstone National Park, in the Sturgis area, and in Milwaukee.

This route travels along the northern portion of the USA. From our start in pretty Portland, we spend 8 days on the road heading to the 81st Anniversary of the Sturgis motorcycle rally. There we’ll spend 2 nights in the area riding the Black Hills, participating in the Biker Belles Celebration, and mingling with the women of Milwaukee. If you’ve never been to Sturgis and want to experience the best of it without any of the drama, then this is your opportunity. After the Biker Belles event, we’ll continue riding to Milwaukee, Wisconsin, home of Harley-Davidson.

We’ll be welcomed in Milwaukee by the Motor Company, with free tours of the Harley-Davidson Museum for our group and DEMO RIDES right here in Milwaukee. At the end of our last day together Harley-Davidson will be hosting us for a spectacular party at MOTOR, right at the heart of the Harley-Davidson complex. You can party heartily on your final day with us because we’ve got transportation for you between the hotel and the party.

Relax, enjoy, meet others, and join the ladies’ motorcycle ride celebration of the year with Harley-Davidson.


  • Portland Launch Party
  • North Cascades Highway
  • Bridge of the Gods
  • Sunshine Mills Winery
  • Lolo Pass
  • An event at the Rankin Peace Center in Missoula
  • Two days of riding in Yellowstone National Park
  • Sturgis Motorcycle Rally – 81st Anniversary
  • Sturgis Buffalo Chip Biker Belles Group Ride
  • Sturgis Buffalo Chip Biker Belles Celebration
  • Riding the Black Hills
  • Needles Highway
  • Mt. Rushmore
  • Devil’s Tower
  • Harley-Davidson Museum Tours
  • Harley-Davidson Demo Rides
  • Harley-Davidson Party at MOTOR
Night Date Start Stay In Miles
1 Saturday, July 31, 2021 ***** Portland, OR *****
2 Sunday, August 1, 2021 Portland, OR The Dalles, OR 112
3 Monday, August 2, 2021 The Dalles, OR Lewiston, ID 263
4 Tuesday, August 3, 2021 Lewiston, ID Missoula, MT 217
5 Wednesday, August 4, 2021 Missoula, MT Butte, MT 159
6 Thursday, August 5, 2021 Butte, MT West Yellowstone, MT 153
7 Friday, August 6, 2021 ***** West Yellowstone, MT 100
8 Saturday, August 7, 2021 West Yellowstone, MT Cody, WY 133
9 Sunday, August 8, 2021 Cody, WY Buffalo, WY 175
10 Monday, August 9, 2021 Buffalo, WY STURGIS 233
11 Tuesday, August 10, 2021 Sturgis STURGIS *****
12 Wednesday, August 11, 2021 Sturgis Murdo, SD 326
13 Thursday, August 12, 2021 Murdo, SD Mankato, MN 364
14 Friday, August 13, 2021 Mankato, MN Milwaukee, WI 359
15 Saturday, August 14, 2021 Milwaukee, WI Milwaukee, WI *****
16 Sunday, August 15, 2021 Milwaukee, WI Ride Home *****

*This itinerary is subject to change.

Chose Your Registration Type

Fully-Guided Registration

Fully-Guided Registration: Ride, Relax, Enjoy!

A ‘done for you’ touring/vacation experience with nothing to do but show up and ride! We’ve got all the logistics covered and will handle all the details and any travel hassles that come up.

Fully-Guided Registration – What’s Included:

  • Event Fee
  • Harley-Davidson Museum Tours
  • Harley-Davidson Demo Rides
  • Harley-Davidson Party at MOTOR
  • Portland Start City Party
  • Accommodations (All hotel rooms)
  • All Breakfasts and Dinners (Except rest day dinners in Sturgis and Yellowstone)
  • Professional Ride Guides who lead you and smooth over any and all obstacles – many are MSF instructors
  • Breakdown Assistance and Pickup
  • Daily Route Briefing with Route Leaders
  • Logistical Support
  • Chase Vehicle Support (We carry your luggage so you only have to ride with layers, a camera, and a bottle of water!)
  • Automatic Check-in at hotels (keys waiting for you)
  • Free Parking
  • Dinner with the main group
  • Free entry to all event activities
  • Roommate matching service
  • Centennial Ride Keepsake
  • Special Surprises exclusively for Fully-Guided Riders

Fully-Guided Registration – What’s NOT Included:

Gas, tips, tolls, incidentals at the hotels, alcoholic beverages, dinners on the rest days, National Parks entry fees and single rooms. Note that the Women’s Motorcycle Conference is NOT included and you will have to register separately for that event on Eventbrite.

Your registration fee includes a $50 donation to Final Salute, Inc., our event charity that supports homeless women veterans.

Single Room = +$1825

Register as Fully-Guided

Self-Guided Registration

Self-Guided Registration: The DIY Pay-As-You-Go Option

If you register as a self-guided rider, then you are completely connected to us yet totally independent…you’ll pay an event fee to participate, then pick and choose what you want to participate in. This way you only pay for what you’re interested in – not the whole shebang.

After you register, we’ll send you a form on which you can let us know what nights you’ll be with us and your billing details, and we’ll send your booking details directly to our hotels (thereby saving you having to call all 11 hotels). They’ll charge you directly for any deposits and fees and you’re responsible for any changes to your reservations. (Note that because we are in some big cities with lots of events going on at the same time as ours you may have to pay a deposit well in advance – our contract with each hotel is different.) We’ve tried our best to negotiate breakfasts to be included in your discounted room rates, but there will be some hotels where we did not (like those $38 breakfast buffets at big-city hotels) so you can make that choice on your own.

Once you’re registered you’ll be able to find your own roommate (if you want one to help reduce costs) in our closed Facebook Group for Centennial Ride riders.

Self-Guided Registration – What’s Included:

  • Event Fee
  • Harley-Davidson Museum Tours
  • Harley-Davidson Demo Rides
  • Harley-Davidson Party at MOTOR
  • Portland Start City Party
  • Hotel Room Reservations (so you don’t have to call all 21 hotels)
  • Route Information
  • Information on and access to any and all “free” events we’ve negotiated along the way
  • Some lunches at dealerships or partner venues along the way
  • Some evening happy hours we’ve negotiated for the entire group
  • Daily Briefings (if desired)
  • Route Book
  • Goodie Bag
  • Centennial Ride Keepsakes
  • Harley-Davidson Museum Tours
  • Harley-Davidson Demo Rides
  • Harley-Davidson Party at MOTOR

Self-Guided Registration – What’s NOT Included:

  • Sturgis Biker Belles Registration
  • Women’s Motorcycle Conference
  • Professional Ride Guides who lead you and smooth over obstacles (most are MSF instructors)
  • Chase Vehicle Support
  • Roommate matching service
  • Tips
  • Incidentals at the hotels
  • Accommodations (Hotel rooms)
  • Meals (some breakfasts are included)
  • Breakdown Assistance and Pickup (we strongly suggest you purchase your own)
  • Logistical Support (You carry all your own luggage and schlep it inside the hotel)
  • Automatic Check-in at hotels (keys ready and waiting for you..you will need to check-in and pay yourself)
  • Parking
  • Any event activities
  • Gas
  • Tolls
  • Alcoholic beverages
  • Other Museum entry fees
  • National Park entry fees

Your registration fee includes a $50 donation to Final Salute, Inc., our event charity that supports homeless women veterans.


(As a self-guided rider you will need to register for the Biker Belles Celebration directly with them if you want to participate.)

Register as Self-Guided

Do you have more questions you need answered before you can register? Be sure to check out our Event FAQ. Still confused? Email Office@WomensMotorcycleTours.com after reading the Event FAQ and we’ll get you sorted out!

Be sure to sign up for email updates because we’ll be adding more experiences and new ways to join and that’s where we’ll announce our live Q&A call-in sessions.