The Berkshire Room (Chicago)

I am in Chicago this week for work and the concierge at the hotel suggested I try the Berkshire Room. So, last night, I grabbed a cab and headed to Ohio Avenue and a bourbon lovers paradise.


The Berkshire Room feels like you are walking into a Speakeasy. It is small, intimate and very well appointed. What makes it even more special is the bartenders know how to create incredible cocktails. On the menu, you can ask for a “Dealers Choice-Cocktail.” It is fun because you pick the glass style, the type of liquor, and your flavor preference – and leave it to the bartender!


I chose a rocks glass and bourbon. They asked what style drink I like and I said I like Old Fashions and he took it from there. What I got was an amazing cocktail made with the following:

2 oz. Ancient Age Bourbon
1/2 oz. Averna
1/2 oz. Walnut Liquor
1/8 oz. House Falernum
Three Dashes of Angostura Bitters
Garnished with an orange peel

I was enjoying the drink so much I decided to order the “Pick Any Tree” Chef’s Rotating Artisan Charcuterie & Cheese Selections with Crostini. It was a generous sized appetizer for two before dinner (I made it dinner). I was enjoying the meat and cheese so much I ordered another “Dealers Choice” to enjoy with it.


I like to sit at the bar, especially when traveling alone. You get a lot of conversation and I tend to learn a lot. Several locals were very knowledgeable about Chicago whiskey bars, bourbon, and the Berkshire Room. I found out it is so popular that two guys got a place very close to the bar so they can have a drink after work on a regular basis.


The Berkshire uses a lot of Buffalo Trace products. They had the full Antique Collection and all years of the Pappy Van Winkle Collection. They had a selection of probably 150 bourbons and ryes behind the bar. They also have a selection of very old bourbons from the 80’s, all the way back to the 40’s.

When in the windy city, stop in The Berkshire Room for a unique whiskey experience. You will be taken back in time. It is a very relaxing experience.

Eating Along the Bourbon Trail

There is no shortage great food in Kentucky and Tennessee (where we began our most recent trip). Here’s a rundown of places we have eaten along the Bourbon Trail.


Martin’s BBQ Joint
We started our trip in Nashville and were really only there the day we arrived. We stayed at the Doubletree right downtown. The staff could not have been nicer and more helpful (you forget how truly heartwarming southern hospitality can be). The concierge gave us several ideas of where to eat, and go for entertainment after dinner.

We decided on barbecue at Martin’s BBQ Joint downtown. The BBQ was incredible. We got the sampler of brisket, ribs, and pulled pork which is served on a big tray with your sides. The have a full service bar so you can get anything you want to drink with your dinner. Coincidentally, the night we were there the local sports station had a satellite broadcast with a couple of Tennessee Titans who were about to play the Patriots for a Super Bowl Berth. After dinner we strolled over to the Tin Roof for some live music and an after dinner drink.

Edley’s Bar B Que  and Jack’s Bar-B-Que
Our concierge at the Doubletree also suggested Edley’s Bar B Que. Others we spoke with suggested Jack’s Bar-B-Que. I don’t think you can go wrong. The BBQ in Nashville is so well known and fantastic. Another place to eat is Acme Feed and Seed for live music and southern fare.

After Dinner
Off to the Tin Roof to listen to some music and have a drink. The bands were good as were the drinks and they were reasonably priced. After Tin Roof we headed to B.B. Kings Blues Club for some blues to finish off the evening. There are so many places to listen to music, stroll around, with the open windows when you hear a band you like pop inside for a drink to relax. The rain which became snow was just beginning as we strolled back to the Doubletree. Reminded me of a Dan Folgelberg song!



OBC Kitchen
We had dinner at OBC Kitchen (“Old Bourbon County”) which was not far from our hotel. That turned out to be a good thing. We were in short sleeves in Nashville the night before and got several inches of snow on our car while dining at OBC Kitchen. OBC has over 400 bourbons behind the bar. If they don’t have it, you didn’t want it anyway. We did not have reservations and when we arrived they said they were pretty full despite the weather. But John Calipari’s table was available since the Kentucky Basketball team was in Nashville. What a treat to sit at the table with his nameplate on it.

The menu at OBC challenges you to tough decisions about what you want to eat. There are so many good choices on the menu it’s tough to pick one. We started with bacon in a glass. Decadent thick sliced honey bourbon sugar glazed bacon. There were 4 pieces served in a tall cocktail glass. This was a meal of its own. I had the cola braised short ribs with grits. Oh my, welcome to the south. We ended with the warm buttermilk donuts, finished with cinnamon sugar. They are served with chocolate ganache, raspberry melba, and salted caramel dipping sauces. You really don’t need the sauces; these donuts stand on their own merit. These are to die for and reminded us of the donuts they serve at the Homestead Resort in Virginia.


Malone’s was another restaurant recommended to us. It is part of the Bluegrass Hospitality Group which also owns OBC. Everyone we spoke with said to go there if you don’t go to OBC. Just looking at the website made me hungry. The original is on Tate’s Creek Road. If you go to OBC and can’t get in there is one a few doors down in the same parking lot.


Brown Hotel
In Louisville there are far too many dining choices. If this is your first trip you must have Louisville’s most famous dish the “Hot Brown” created at the Brown Hotel in the 1920’s. Go for lunch or dinner to have a hot brown. It’s open faced turkey served on oven browned bread, covered in a mornay sauce, bacon and sliced tomato. It is then browned on top in the oven. Worth every calorie, worth the wait.

The Seelbach Hotel

We decided this trip we wanted to eat at dinner Milkwood. Chef Edward Lee merges Southern food with Asian flavors and bourbon cocktails at this hip venue. Lee collaborated with Jefferson’s distillery to help create the “Chef’s Collaboration Bourbon.” He wanted a bourbon he could serve with his spicy dishes. A lot of very creative dishes, and fun environment. Lynn had the sorghum glazed rabbit and I had the pork shoulder. Both were excellent, very creative, very fun. This is the last thing you would expect on Main Street in Old Louisville. We had a wonderful experience.

The Silver Dollar
After dinner we took a cab to Silver Dollar. Everyone we spoke with said you had to go there for a drink. A little loud for my taste but they have an amazing bar. What impressed me was they have vintage whiskey as old as 1941. I tried a 1986 Sunny Brook Bourbon. It was only $25 for a pour and well worth it for the experience, it really was ethereal. Older bourbon has a unique taste everyone should experience. You can also get southern classics here lick chicken and waffles, baby back ribs, and a fried oyster sandwich.

The Silver Dollar Bar

Proof on Main

For lunch in Louisville I recomend Proof on Main. It in the fun 21c Museum Hotel. As we were walking by there was a little boy playing with one of the big red penguins in the window. They have a great bar and locally sourced southern fare.


I could recommend 30 restaurants in the cities we visited, and there are so many good places to eat. I haven’t had a chance to experience many of the new ones. Definitely try local restaurants and something new when you’re travelling along the Bourbon Trail. This is about the experience and pleasures all Kentucky and Tennessee. Most of all don’t worry about the calories. “The Diet starts next week,” you are in the south, enjoy every minute.