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Scenic Guided Motorcycle Tours Across The United States

Sturgis/Yellowstone/Glacier NP Guided Motorcycle Tour

The Sturgis/Yellowstone/Glacier NP Motorcycle Tour is from July 31 thru August 15th.

Motorcycle Tour Description

This tour starts on Friday at 6:00 AM at a restaurant in the western suburbs of Chicago.  This is earlier than our typical starting time because of the distance we need to travel on the first day. Over breakfast we will get acquainted with the other riders in our group. After breakfast, we will have a briefing on the day’s ride and on the safe riding practices we will be using during the entire tour. We will specifically cover safe riding techniques and group riding hand signals. This should be completed before 7:00 AM so we can begin our adventure with “Kick stands up” (KSU) at 7:00 AM.

If you have ever traveled between Illinois and South Dakota you know that there is very little to see along the way until you get into central South Dakota. We will be taking interstate highways most of the way to our destination but we will be taking frequent breaks. We will also ride the posted speed limit per my GPS.  We understand that this may be more miles than you normally may ride but if you prepare yourself and your motorcycle you will be able to make it with little difficulty. Our first night will be spent in Sioux Falls, SD.

Day 2 – the fun really starts. Our first stop in the morning will be in Mitchell.  After gas and a pit stop we will make a visit to the famous Corn Palace. We will break for lunch mid-day and then arrive at the Badlands National Park several hours later. We will ride through the Park and see the amazing geological formations. Everyone has to stop and see the famous Wall Drugs. This will be our last stop before we reach our hotel later that afternoon.

We will spend the next 4 nights in the same hotel in Keystone, SD Keystone is about an hour south from the town of Sturgis. The advantage of staying that far away from Sturgis is that the town is less crowded, we can walk to nice restaurants, bars, and casino near our hotel and we can ride all the great roads in the Black Hills before the crowds from Sturgis get there. We will go into the town of Sturgis at least one time, to see all the craziness, and for many people that is more than enough. Here is a brief summary of the riding we will do all week:

Friday – Ride Illinois to Sioux Falls, SD

Saturday – Corn Palace/Badlands/Wall Drugs/Keystone

Sunday – Ride to Deadwood and Sturgis

Monday – Custer State Park and Wildlife loop

Tuesday – Needles Highway, Mt. Rushmore

Wednesday – Devil’s Tower/Spearfish Canyon/Sheridan Wyoming

Thursday – Bear Tooth Pass, Chief Joseph’s Highway/Cody

Friday – Yellowstone National Park/West Yellowstone

Saturday – Yellowstone NP/Helena Montana

Sunday – Whitefish Montana

Monday – Glacier National Park/Great Falls, Montana

Tuesday – Bismarck, North Dakota

Wednesday – St Cloud, Minnesota

Thursday – Ride the Great River Road/ Prairie du Chien

Friday – Return to Chicago Area

We will typically ride 175 – 225 miles each day while in the Sturgis area. I can tell you that you will have a great riding experience and if you are a novice rider you will become a much better rider from the riding experiences on this trip. If you wish to go to the campgrounds such as the Buffalo Chip or to the Glencoe you can attend these venues on your own!  If you ride with us, as always you must adhere to our no drinking policy while riding.

On Wednesday we will pack up and leave Keystone for Devil’s Tower, Hewlett and Sheridan, Wyoming. While this is a longer riding day it is a very easy ride. Since there are very few roads in this part of Wyoming we will be riding some interstate highway.

Thursday will be an amazing riding day. We will ride some roads many have only read about in magazines. We will start our day with a ride over the Big Horn Mountains, followed up with Bear Tooth Pass and finally Chief Joseph Highway before we reach Cody. During the summer there is usually a rodeo each night and the museum is a great place to learn much about the exploration and history of the area.  We will sleep in a little later the following morning so enjoy Cody and what it has to offer!

Yellowstone is a place I have had the opportunity to visit many times in my life and I always find it one of the most beautiful places on earth. We will spend the next two days riding around the park and looking at the amazing sights. We will spend the first night in West Yellowstone and then Bozeman.

We will leave Bozeman and head north toward Glacier National Park. This will be just another day of great riding in Montana. We will spend the night in Whitefish Montana.

Today we ride to Glacier National Park. Many do not ride to Glacier NP because of the distance and time it takes to get there. You will be glad you took the time to see the incredible beauty of the park, words and photos do not do it justice. You must see it for yourself! We will send the night in Great Falls, Montana.

The next few days we will ride across Montana, North Dakota and Minnesota with frequent stops for breaks and sights along the way. You will understand why Montana is called “Big Sky Country” and why Minnesota is called the land of 10,000 lakes. We do not know what North Dakota is called!

The next two days we will spend riding along the “Great River Road”. You may be anxious to get home but riding along the Mississippi River in Minnesota, Wisconsin, and Iowa is extremely enjoyable.

We will spend our last night together in Prairie du Chien, Wisconsin. We will have the opportunity to talk about our last 2 weeks of riding and the sights and places we saw along the way. You will start thinking about our last day’s ride home and how quickly the 2 weeks went.

After breakfast we will continue back along the Great River Road on the Iowa side near the town of Millville, Iowa. A short ride to the river where we will load the motorcycles onto a river ferry boat. If you have never crossed a river with your motorcycle you are in for a real experience. We will arrive in the Chicago area later in the afternoon.

We created this tour because just one week in Sturgis and back home was not enough. We decided to give riders the opportunity to see Yellowstone and Glacier National Parks and so much more. You will experience the summer heat of the prairies and cool temperatures of the mountain ranges. Packing your bike will not be too difficult as we will have a support vehicle to carry our luggage and that weary passenger who just wants a break. We guarantee this will be one of the most memorable rides you will ever make. Like all our tours, space is limited so contact us and reserve your place today!

Motorcycle Tour Payments

We offer the ability to pay in installments for all tours but they must be paid in full at least 30 days prior to the tour start date. If we purchase your airfare it must be paid at the time of booking and will be charged to your credit card. We will continue to offer customized tour packages for individuals, groups or organizations. If you are planning a business conference this winter in warm places such as Arizona, we can arrange a group outing for you and your colleagues that would include rental motorcycles.

Please Note!! All tours include your lodging! The "Ship, Fly and Ride" tours include shipping your bike round trip and your lodging! Rental motorcycles are available through Harley-Davidson Authorized Rental Dealers! Our 3-day weekend tours include lodging and all meals. Tours also include at least one group dinner, most breakfasts, route sheets, guides and much more.

Tour On Two offers a great motorcycle riding experience at a great price!

What Our Riders Say About Tour On Two...

“Great tour! Bill Gade bends over backwards, from planning to the actual trip, to show us a wonderful and interesting time. Great value for the money.” Tom S.

Motorcycle Tour
Details & Pricing

July 31 - August 15th



Ride Days/Miles



Most Breakfasts/3 Dinners





Rental Motorcycle & Insurance


Fuel For Rental Motorcycle


Rider Shared Room


Ride Private Room


Rider with Passenger


Rider Skill Level

Not Included

Tolls/Park Entrance Fees

Not Included



Motorcycle Transport

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