Top
Ole Shenandoah Cheroots Bootlegged Cigars
  • Ole Shenandoah Cheroots Bootlegged Cigars
  • Ole Shenandoah Cheroots Bootlegged Cigars
  • Ole Shenandoah Cheroots Bootlegged Cigars
  • Ole Shenandoah Cheroots Bootlegged Cigars
Click the icons below for product information.

Ole Shenandoah Cheroots Bootlegged Sale

Pack of 40

You sure can root for these! 

Listen, you might call me crazy, but these Ole Shenandoah Cheroots are one of my absolute favorite cigars to come through the office in years. But before I get into that, let’s get a few things out of the way. 1.) These are not fancy cigars. 2.) They are not pretty. They’re cheroots — rustic, old-school, and gritty. But they taste awesome and burn well, and that’s what really counts. 

Featuring a Pennsylvania Broadleaf wrapper and tons of unique smokiness, each one of the undeniably American offerings in this trilogy is the perfect option for someone seeking a quick, 15-minute bout of deliciousness. I’ve burnt through pack after pack of each option on long commutes, late nights, and early mornings – and I’m ready to declare it now: these are THE best cheroot money can buy. Get some! 

Bootlegged: Flavored with rum, Bootlegged amps up the spice factor.


Size
PackIn StockMSRPPriceQtyCart
Bootlegged (Cigarillos) (4.0"x28)
Pack of 40In Stock$55.00
save $42.5077% off
$12.50
Overall Rating4.32 out of 5 Based on 44 Ratings

Customer Reviews of “Ole Shenandoah Cheroots Bootlegged”

Write A Review
5 out of 5
5 Star
24
4 out of 5
4 Star
12
3 out of 5
3 Star
6
2 out of 5
2 Star
2
1 out of 5
1 Star
0
Showing 1-44 of 44 Reviews
5 out of 5
Tastes AND smells awesome! Yup, these win!
Bootlegged tastes and smells awesome! What a great little smoke. CI wins again!
4 out of 5
Ole Shenandoah
Taste and great price
5 out of 5
Great Cigars.
Great Cigars. Way better than Backwoods which I used to buy before their price went up and quality went down. The Ziploc pack they come in is very nice also to keep them fresh longer. Great quality.
5 out of 5
cheroot
there great
4 out of 5
Great flavor.
Great little cigars for when you have much time.
5 out of 5
Ole Shenandoah
Good price good flavor pleasant smoke
5 out of 5
Great Casual Cigar
Perfect for a commute or a short smoke, love these, I keep them next to my humidor.
4 out of 5
OleShenendoacheroot.
Nice smoke if you just have time to enjoy a short cigar . I’d say you should try these.
5 out of 5
great value
best small smoke for my drive home from work
4 out of 5
Go to cigarillo
Channel your inner Clint Eastwood and buy these. My go to cigarillo.
5 out of 5
Drive home
Best way to end your day, price and reusable pouch. Super value.
5 out of 5
nice aroma great price
nice quick flavorful cigar
3 out of 5
Not bad
Not bad
4 out of 5
smooth smoke
good fresh cigar great value for the money if I can't get backwoods this is a good alternative
5 out of 5
Great little smokes!
Great taste, great fragrance, great construction! Simply Great!
5 out of 5
Great little smoke
Burns even, smokes smooth, and tastes great. What more could you ask of a 15 minute cigar!
3 out of 5
Bootlegged cheroots
Real loose on one end. Burned fast. Flavor good.
3 out of 5
Is not my favorite but
Is not my favorite but is an ok cigar, definitely not like the bandidos.
5 out of 5
Great
Cheap price. Great taste. Doesn't burn hot. I was holding my breath when I bought these, and I couldn't believe how good these are. I can't wait to try the other flavors.
5 out of 5
Found my fix!
Ive finally found a cigar that closely smokes and tastes like a backwoods Black and Sweet! The cigar that I was so addicted to! They quit offering them last fall after the hurricane in Puerto Rico and still are not to be found on any cigar website anywhere! These Ole Shenandoah Bootlegged cigars, are the closest tasting and smoking cigar, Ive found since. The wrappers are actual leaf rolled like the backwoods, but they are just a tiny bit smaller in diameter (Not much tho!). I give 5 stars because I have bought several different brands to find I wasted my money, and these will replace my craving for the Backwoods!
3 out of 5
Switchback
I tried the Ole Shenandoah because they were out of the Backwoods that I normally buy. Compared to the Backwoods, it was a smaller cigar with less sweetness. It's not a bad smoke, but I'll switch back to Backwoods.
5 out of 5
Good flavor'
Good small cigar for a short break. Bootlegged was good, have to try the others.
5 out of 5
Top notch
A friend brought some of these to our weekly cigar day. The “bootlegs” are my current favorites full of sweet flavor at a absolutely great price. Give them a try you will not be disappointed.
5 out of 5
Spaghetti Western
No need to wear a cowboy hat, but you do feel like you should be in a spaghetti western and have Clint Eastwood riding on a horse. The smoke is very mild and delightful. Burns slow and even. A little messy you will be spitting a bit but don’t all westerns spit. 😀
4 out of 5
Backwoods are better
Backwoods are better
5 out of 5
Delicious
I really liked the tummies little treats. I hope I can get more special deals like that one.
4 out of 5
Pretty good
These are pretty good cheroots. They smell fantastic and smoke smooth. I like the bandidos better but these are good for a change.
4 out of 5
Ole Shenandoah,Bootlegged
They may be homely,but they taste pretty good!I haven't gone through all of them yet,but so far only had trouble with one(hard drawing).If you want a quick no frills smoke,I'd recommend you try these out.
4 out of 5
Like them
Good cigarillo for the money. Great quick smoke for when you don't have a lot of time
5 out of 5
Bootlegged Cheroots
They’re ugly, a little loose, but, just a pretty darn good smoke, great aroma and everyone of um are the same, very consistent. Definitely would recommend for a quick smoke
3 out of 5
Good for when you only
Good for when you only have ten minutes to smoke, and unlike some other small cigars, you don’t have to relight them a dozen times.
4 out of 5
Ole Shennendoah
Not a bad 15 minute smoke for the money.
3 out of 5
Good 15 min cigar
Good 15 min cigar
5 out of 5
Excellent short smoke
These rough little buggers are great for a quick break. Good tasting and mild.
5 out of 5
Great little smoke
I have been looking for a good little smoke. I found it.
2 out of 5
Standard stuff
Not much different from Backwoods or that green-pack brand. This style “cheroot” just isn’t that good.
5 out of 5
Old Shenandoah
Nice sweet taste, pleasant aroma. Lit easy, drew easy. Nice white smoke. Great when all you want is a 15 min smoke
5 out of 5
Last Order
The cheroots i bought are very flavorful and enjoyable. They were the Ole Shenandoah's.
5 out of 5
Kinda like backwoods
These are similar to woods but there a little thinner leaf but they unravel nicely
5 out of 5
Cheap, flavorful short smoke.
Bootlegged is my favorite. Just right combination of medium-bodied tobacco satisfaction with just a hint of sweet spiciness.
4 out of 5
Ole Shenandoah Cheroots
I was pleasantly surprised to find this cheroots flavors to be mellow and it's a great smoke for not much money. I definitely recommend it for a quick smoke.
4 out of 5
Cheroots
Burns and smells like old fashioned pipe tobacco. For a quick smoke with taste it's a winner. Better then any flavored cigar out there for taste. Burns well, for short fillers and pieces. I will reorder again. Wife loves them!
5 out of 5
Great for the price
Cannot beat these for the price and great if you just want a quick smoke or are short on time.
2 out of 5
Not for me
I ordered these as an alternative to Bandidos which have been tough to get as of late...they arrived quick as usual from CI but the flavor was just not for me...a little to chocolatey tasting for my taste