A Blues Highway Itinerary by Train

My first trip as a travel blogger was way back in 2009. I traveled the Blues Highway by train.

My brother has frequently been at me to write up this solo travel itinerary so that others can enjoy it without doing all the planning.

I had thought that it was too late. Too much time had passed and the information would not valuable to you. But thanks to submissions from readers to both the Solo Traveler Accommodation Guide and the Destination posts it can be done properly.

Yes, I am finally getting around to providing my Blues Highway itinerary.

Blues Highway Itinerary by Train

The City of New Orleans is the name that has been given to    Train 59 which runs from Chicago to New Orleans and, of course, back again. I traveled from north to south after getting myself to Chicago by train. I flew home from New Orleans.

As you can see from the list, the train has many stops along the way. I only had nine days (two weekends plus the Monday to Friday in between) so I chose to make two stops between Chicago and New Orleans, in Memphis and Jackson. If you were to make the trip non-stop, it’s a  19-hour journey. I would definitely recommend stopping in Memphis. I would consider Jackson to be optional. Train 59 has a Dining Car and a Cafe Car and runs seven days a week. You can download the city of New Orleans Route Guide here.

Here's my recommended itinerary. Look below for where to stay and what to do.

Chicago – Arrive early day 1. Spend two nights (3 days) and leave late on day three taking the overnight train to Memphis. Departs Chicago at 8:05pm. Arrives in Memphis 6:27am.

Memphis – Spend 2 nights (2 days) and then take the train to Jackson. Departs Memphis at 6:57am. Arrives in Jackson at 11:12am.

Jackson – Spend 1 night (1 day) and then take the train to New Orleans. Departs Jackson at 11:20am. Arrives in New Orleans at 3:32pm. If you have more than nine days, spend an extra day in Jackson, rent a car and follow the Mississippi Blues Trail.

New Orleans – Spend 2 nights (3 days) and then fly home late on your day.

Three Days in Chicago

Get to Chicago as early in the day as possible so that you have as much time as possible in this fantastic city.

Where to stay.

I stayed at the Hotel Monaco on Wabash Ave. It looked like a typical boutique hotel in the lobby but when I got to my room I couldn’t believe it. It was theatrical, full of reds and golds, with unusual accents. When I opened the drapes to see what kind of view I had, I discovered a huge window seat overlooking the Chicago River. For budget options, readers have suggested IHSP Chicago Hostel and Chicago Getaway Hostel.

What to Do.

• Book a Greeter. The Chicago Greeter program is excellent. I booked a Greeter and asked for a bicycle tour. I rented the bike from Millennium Park and we covered the waterfront, traveled up to Wrigley Field and then back to Millennium Park through interesting neighborhoods. Your Greeter is free but it's nice to make a small donation to the organization.
• Take an architectural tour. Chicago is known for its fabulous architecture and a great way to see it is by one of the tours up the Chicago River. The Chicago Architecture Foundation offers a river cruise and other options.
• See the city in the day, at night, from the river… It's not often that I might want a two-day Hop-On, Hop-Off tour package but in Chicago I think it's a good deal. With it you can do the usual daytime tour plus a river tour and a night tour.
• Go to Frank Lloyd Wright house. Take public transit to the Frank Lloyd Wright Home & Studio. The Frank Lloyd Wright Trust has many options.
• If you're a museum goer you might want to get a CityPASS.

Where to Find Blues and Jazz.

• Kingston Mines seems to be the local favorite and it was certainly mine. The club turns 50 next year. Kingston Mines has two stages going all evening. When one band goes on break, the audience moves to the other room where another is ready to play – and then back again.
• Also recommended though I have not been are
  • Blues Heaven Foundation
  • Rosa's Lounge

Two Days in Memphis

Where to stay.

I stayed in a magnificent mansion B&B that is now closed. So I've done some research for you. Depending on my budget, these would be my choices.

• Luxury near Beale Street. The Peabody Memphis is the city's grand old hotel and just a block from Beale Street.
• Near Graceland. Days Inn Memphis at Graceland is a walk to Graceland but a 15-minute taxi ride to Beale Street.
• Hostel Memphis. This is the only hostel I found in Memphis. It's located in the Cooper Young area which is a vibrant midtown neighbourhood with shopping and restaurants.

What to do.

• Go to Sun Studios. Sun Studios declares itself as the “Birthplace of Rock N' Roll!” given that Elvis Presley, Johnny Cash, Carl Perkins, and Jerry Lee Lewis all did their first recordings here.
• Visit Graceland. This is Elvis Presley's legendary home. The tour of Graceland was absolutely a highlight of my time in Memphis.
• Take in the National Civil Rights Museum. Located at the Lorraine Motel where Dr. Martin Luther King Jr. was assassinated, the very powerful National Civil Rights Museum shows the struggle from the early days of slavery through the civil rights movement. The Museum will observe the 50th Anniversary of the death of Dr. Martin Luther King Jr. in a yearlong commemoration from April 4, 2017 to April 4, 2018.
• Enjoy the South Main Arts District – The South Main Arts District is the area for restaurants, boutiques, cafes and nightlife.
• Stroll along the Mississippi. You'll be seeing the mouth of the Mississippi in New Orleans but in Memphis you can get a feel for what the majority of this magnificent river is like.
• Explore the Murals. Here's a post from the I Love Memphis blog that will tell you how. Go through the blog to learn more about Memphis.
• Check out the events going on when you'll be there. Here's a What's On list.

Where to Find Blues and Jazz.

• Beale Street. BB King's (a classic), and Handy Park are two of the tops for Beale Street but there are many other options as well. If you want you can spend all your time cruising Beale Street and get your fill.
• Wild Bill's at 1580 Vollintine Avenue
• Find the best music for your time there. Check out the Listen Up series on I Love Memphis. Every month blogger, Holly Whitfield, tells you the places to go for music in her city.

One Day in Jackson, Mississippi

I don’t usually go to bars every night of the week so by the time I got to Jackson I was getting tired. I took a day off to relax and The Fairview Inn was the perfect place. When I asked for recommendations for a Blues club everyone from the cab drivers to the innkeeper suggested 930 Blues Café. And it was my favorite of my entire trip. Unfortunately it's now closed. So I called the Fairview Inn to find out where they are now sending their guests for great live music. The answer is below.

Where to stay.

• Luxury accommodation in Jackson. I would definitely recommend The Fairview Inn.
• I'm afraid that I can't really recommend an option because I don't know the city well enough. In this case I would likely choose a chain hotel based on my budget.

What to do. 

If you follow the itinerary above, you'll arrive at 3:30pm one day and leave the next at 11:20am. That's not a lot of time. You could take this day as a quiet day as I did or you could take in the following.

• Interested in history? You are in the capital of Mississippi so, of course, there are a number of museums including the Old Capitol Museum.
• An amazing gallery. The Mississippi Museum of Art.
• Distillery tour. Cathead Distillery offers tours and tastings of their vodka distillery every Thursday and Friday from 3pm to 6pm and Saturdays from 1pm – 6pm.

Where to Find Blues and Jazz

• Underground 119. Located underneath the century-old Elks Club Building in downtown Jackson, Underground 119 offers music every Thursday through Saturday. I called the Fairview Inn that directed me so well to 930 Blues Café and was told that is the place that everyone is excited about in Jackson.
• Duling Hall. Duling Hall is a concert venue located in a former elementary school built in 1928. To give you a sense of the type of musicians they bring in, The Bacon Brothers (Kevin Bacon and brother, Michael) are booked in for June 12th.
• Cathead Distillery. After a tour of the distillery (see above for their tours) stay for one of their concerts. Here's a link to their schedule.

Three Days in New Orleans

Where to stay.

• A boutique hotel. International House is, as the French say, tres chic. It's within walking distance of the French Quarter but offers a sophisticated escape from the busy portion of the city.
• A hostel. IHSP French Quarter House is a top-rated hostel.
• B&B. Madame Isabelle's House is both a B&B and a hostel with a shared kitchen available.

What to do.

• Eat beignets. Drink Cafe au Lait. The classic place for each is Cafe Du Monde which happens to be at the market.
• Got to the French Market. Open daily from 10am to 6pm the French Market offers 3 centuries of history and 6 blocks of shops.
• Wander the French Quarter. Here's a list of French Quarter highlights.
• Ride the St. Charles streetcar. Take the St. Charles streetcar which starts just outside the French Quarter on Canal street. It travels uptown through the Garden District and historic mansions, past the Lafayette Cemetery (one block off the route), Audubon Park which includes a zoo and ends at Palmer Park very near to the Camellia Cafe which I went to and thought was okay. Many people rave about it. It's 90 minutes round-trip. City passes for buses and streetcars are super cheap if you buy them online.
• Take a swamp tour. I had never been to country like this before so it was fascinating unto itself. Add the excitement of looking for and finding alligators and swamp tours make for great day trips out of New Orleans.
• What readers recommend. Here's a link to a post featuring two readers' recommendations of NOLA.

Where to find blues and jazz.

• Preservation Hall. This club is credited with keeping jazz alive. There's no bar. No air conditioning. It's all about the music. Shows nightly and it's open to all ages.
• Frenchman Street. Snug Harbor is supposed to be the place to go but it’s layout didn’t work for me as a solo traveler. I went across the street to Jimbeaux’s which is now closed. Look for a small venue which you'll likely find to be more friendly.
• Royal Sonesta Hotel. The Jazz Playhouse is an upscale club at one of the finest hotels on Bourbon Street. Shows start at 8pm and there is a one drink minimum purchase per set.

I finally did find one place I loved on Bourbon St.: Irvin Mayfield’s Jazz Playhouse at the Royal Sonesta Hotel. It was my one exception to the seedy bar scene. I enjoyed great jazz in an upscale club where I had a bite to eat and two drinks for under $30.

What's Missing? Restaurants and Where to Eat

As I said at the start, I made this trip in 2009. That's too long ago to be able to suggest restaurants and the like. Perhaps you can make recommendations in the comments.