Top
Click the icons below for product information.

Ole Shenandoah Cheroots

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! 

Original: The OG. Rich, smooth, and flavorful with a fantastic aroma.
Bootlegged: Flavored with rum, Bootlegged amps up the spice factor.
Appalachian Harvest: Lightly berry flavored, these are a great combination of smoky and sweet. 


Size
Pack In Stock MSRP Price Qty Cart
Appalachian Harvest (Cigarillos) (4.0"x28)
Pack of 40 In Stock $50.00
save $27.5055% off
$22.50
Bootlegged (Cigarillos) (4.0"x28)
Pack of 40 In Stock $50.00
save $27.5055% off
$22.50
Original (Cigarillos) (4.0"x28)
Pack of 40 In Stock $50.00
save $27.5055% off
$22.50
Overall Rating 4.17 out of 5 Based on 65 Ratings

Customer Reviews of “Ole Shenandoah Cheroots”

Write A Review
5 out of 5
5 Star
31
4 out of 5
4 Star
18
3 out of 5
3 Star
12
2 out of 5
2 Star
4
1 out of 5
1 Star
0
Showing 1-50 of 65 Reviews
4 out of 5
Ole Shenandoah
Much better than Backwoods priced right
4 out of 5
Nice quick cheroot smoke
Full flavored, nice draw and for the money good buy.
3 out of 5
Shenandoah harvest
Decent product, had a funk to the taste on these harvest series, burns well but, I’m sticking with backwoods, they’re worth the price
5 out of 5
Great
Great
5 out of 5
Drive home
Best way to end your day, price and reusable pouch. Super value.
3 out of 5
Ole Shenandoah vs Backwoods
Took about 3 packs but just as good as Backwoods. Two issues with Backwoods. Many are not smokable and cost. Very few throw-aways with these and MUCH cheaper. Just a decent quick smoke.
2 out of 5
Shenandoah Cheroots
I like Cheroots, but these are not to my taste. Pretty dry feeling in my mouth.
4 out of 5
Similar to Backwoods
These are very similar to Backwoods. They work well as a temporary replacement
5 out of 5
nice aroma great price
nice quick flavorful cigar
3 out of 5
Not bad
Not bad
4 out of 5
Not bad.
I like them better than backwoods but not as much as ugly coyotes, which are out of stock again.
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!
2 out of 5
A little harsh
A little harsh
3 out of 5
Bootlegged cheroots
Real loose on one end. Burned fast. Flavor good.
3 out of 5
These have not much flavor
These have not much flavor as Backwoods but never a problem of clogging or being dried out
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
Satisfied customer
They are a very nice, smooth and flavorful little cigars. Different flavors to choose from. I am very pleased with them.
5 out of 5
great
good little smokes that burn well to the end
5 out of 5
Great smoke for the price
Get little smoke for on the go...
3 out of 5
Lacking
Poorly wrapped and a bit harsh. Not what I had hoped
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.
3 out of 5
Mehhh
They were a Lil bland and dry. I will not reorder them.
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
short and mellow
This is a good short smoke that is mellow and smooth. Just right with a cup of coffee.
5 out of 5
Perfect
Just the right amount of sweet !
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.
4 out of 5
Cheroots shanandoah
Nice little tasteful cigar nice cold weather cigar for outside when it's to cold to smoke a big one.
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. 😀
3 out of 5
Typical Cheroot short and sweet
Purchased the Appalachian Harvest and the Originals and found the flavor profiles to be similar in taste. Bought on the recommendation of CI profiler that stated Cheroots that actually burn good. I found the burn to be like others in this class of cigar in that you will need to relight often. That being said, the cigars are not bad. If you like this type of cigar give them a try.
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
Good change
Not a bad little cigar for the price. If you like Backwoods and want to save a few bucks give these a try. I don't think they're made as well but they smoke and taste just fine.
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.
4 out of 5
Good short smoke.
Full flavor but not too harsh like many other brands. Hint - bootleg is even better.
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
Much better Quality than backwoods!
For the price these are great cigars. They are consistent also unlike backwoods that I used to buy that always had at least one bad cigar rolled too tight in every pack.
4 out of 5
Nice
Nice quick, tasty little smoke. I’m looking forward to trying the flavored ones.
5 out of 5
Tasty quick smoke
A sweet cheroot that burns nicely. Even draw every time and comes in it's own reseal able little pouches.
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
Appalachian Harvest
A nice, sweet smoke, tasty, smooth, and great when you don't have a lot of time.
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
Good Smoke
Very tasty cheroot. I like them better than Backwoods as they are constructed much better. Will be buying them again.
4 out of 5
Holds it's own with cigarillos twice the price
Original holds up for satisfying medium-bodied flavor in a short smoke. Perfect for a quick break from the cubicle or watching the sunrise with your morning coffee.
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
This cigar was a nice
This cigar was a nice smooth smoke. Will order them again after completing my Victor Sinclair cigarillos.
5 out of 5
AWESOME
Tastes Great, just wish I could get them from my local store..
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.
5 out of 5
Loved it
Nice Smoke
4 out of 5
Jamie
Smooth yet strong
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