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OriginDominican Republic
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Ole Shenandoah Cheroots

4.4 out of 5170 Ratings
5 out of 5
5 Star
95
4 out of 5
4 Star
52
3 out of 5
3 Star
19
2 out of 5
2 Star
4
1 out of 5
1 Star
0
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Profile
ShapesCigarillos
WrapperMaduro
OriginDominican Republic
More Details

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. 


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Size
Pack
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MSRP
Price
Qty
Cart
Profile
Shape
Cigarillos
Wrapper
Maduro
Origin
Dominican Republic
Flavored
True
Pressed
False
Has Tip
False
Filler
Dominican
Sweet
False
Appalachian Harvest (Cigarillos) (4.0"x28)
Shipping Constraints
Pack of 40
In Stock
$55.00
| save $28.01 51% off
$26.99
Profile
Shape
Cigarillos
Wrapper
Maduro
Origin
Dominican Republic
Flavored
True
Pressed
False
Has Tip
False
Filler
Dominican
Sweet
False
Add To Wish Lists heartheart
Profile
Shape
Cigarillos
Wrapper
Maduro
Origin
Dominican Republic
Flavored
True
Pressed
False
Has Tip
False
Filler
Dominican
Sweet
False
Bootlegged (Cigarillos) (4.0"x28)
Shipping Constraints
Pack of 40
Backordered
$55.00
| save $28.01 51% off
$26.99
Profile
Shape
Cigarillos
Wrapper
Maduro
Origin
Dominican Republic
Flavored
True
Pressed
False
Has Tip
False
Filler
Dominican
Sweet
False
Add To Wish Lists heartheart
Profile
Shape
Cigarillos
Wrapper
Maduro
Origin
Dominican Republic
Flavored
False
Pressed
False
Has Tip
False
Filler
Dominican
Sweet
False
Original (Cigarillos) (4.0"x28)
Pack of 40
In Stock
$55.00
| save $28.01 51% off
$26.99
Profile
Shape
Cigarillos
Wrapper
Maduro
Origin
Dominican Republic
Flavored
False
Pressed
False
Has Tip
False
Filler
Dominican
Sweet
False
Add To Wish Lists heartheart
Shipping Constraints:
  • These items cannot be shipped to Massachusetts state addresses.
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overall rating 4.4 out of 5 True { } True { } True { } Based on 170 Ratings
Customer Reviews of "Ole Shenandoah Cheroots"
5 out of 5
5 Star
95
4 out of 5
4 Star
52
3 out of 5
3 Star
19
2 out of 5
2 Star
4
1 out of 5
1 Star
0
Write A Review
Showing 1-50 of170 Reviews
4 out of 5
These are a good every day cigar. Good draw, the rum flavor is almost nonexistent and leaves a sour after taste on the mouth. It does have a good slightly sweet smoky flavor. CI has really good customer service!
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5 out of 5
Great little stogie for when in out riding scoots with friends. Excellent taste, draw & burn. Aroma is excellent! Effortless pull!
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5 out of 5
Great for when time doesn’t allow for relaxing with a regular cigar. Great flavor
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4 out of 5
Good draw, good taste, good aroma, good burn, good price. Really ugly.
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5 out of 5
Amazing flavor easy burn when you don’t have time to smoke a full stick. Or even on their own great smoke
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4 out of 5
Great price and great taste
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5 out of 5
Great cigar
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5 out of 5
Good taste, Good draw, ergo, good smoke.
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5 out of 5
I've tried several cigarillos and cheroots because I rarely have time for an hour-long smoke, and these Bootlegged are my go-to. The flavor is phenomenal and consistent. They don't get harsh and stay sweet to the end. And best of all, that dull, stale aftertaste you're used to from every other machine-rolled smoke you've ever had, well that's gone with these. It's pretty amazing for the price. There are some premium hand rolled cigarillos that come in tins like Cohiba and Davidoff that are probably a little better, but not near enough to justify their extravagantly higher expense. You will occasionally get one with a hard draw that won't stay lit, but it's rare. For the money, these are unbeatable.
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5 out of 5
They taste great with a nice slow burn. Perfect size to grab one and sit down. They sell out so I also think that speaks in itself!
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5 out of 5
Good stronger flavor
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5 out of 5
Billed as the best Cheroot for the $$$; and they just might be...
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3 out of 5
Good taste ,cheap price and most are wrapped just right some are tight and draw hard but most are good
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5 out of 5
Very good daily smoke.
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5 out of 5
Very nice smell, a bit like pipe tobacco.
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5 out of 5
A GREAT smoke at a reasonable price!!
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4 out of 5
A tasty little smoke when you don’t have the luxury of time to enjoy one of its big brothers. A bit rough in appearance but the beauty is in the smoking. So close your eyes and enjoy!
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5 out of 5
We're both great for the price
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5 out of 5
I can't claim to be a cheroot aficionado; however, I really enjoy these sticks. It pains me to grab $5+ stick from humidor when I have <30 minutes. I've also tried big name $20+ tins for this time crunch exercise. For the $$, I'll take these.
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5 out of 5
Outstanding service. Product as described.
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4 out of 5
Good little cheroot for the price .
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4 out of 5
Good little quick smoke . Burn well good flavor . I would buy these again
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4 out of 5
These are a nice quick smoke with mild flavor and easy draw. They are rolled much better than the twiggy Backwoods brand.
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4 out of 5
I bought these sp that I could enjoy a quick smoke. Turns out, I really like them! They do have a great aroma and flavour. They are "rustic" in wrapping and appearance, and I guess that's what a cheroot should be!
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5 out of 5
Pleasantly surprised with these sticks! Flavor, style, and packaging identical to Backwoods, but so much more of a pleasant experience. If you smoke Backwoods or other ' rough cut' smokes, you owe it to yourself to buy these!
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4 out of 5
The perfect go to for a quick smoke. Nothing fancy, nice bit of flavor, a great 10-15 minute smoke.
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5 out of 5
Excellent cheroot. Just right for a quick smoke.
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5 out of 5
Very smooth and flavorful, and I like the ziplock style packaging
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5 out of 5
Ole Shenandoah Cheroots Appalachian Harvest are a nice short smoke with a touch of sweetness. The re-sealable pouch is a nice feature too.
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4 out of 5
I have only purchased these a couple of times, mainly for a sort term smoke around the house. Really enjoy them.
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5 out of 5
My everyday smoke. Love the resealable foil pouch.
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4 out of 5
I bought these especially for those cold days when I can't take the time for a full sized cigar. I like the taste and quality of these small smokes.
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5 out of 5
The Ole Shenandoah Cheroots Bootlegged are my favorite short smokes. My long smokes are split between the Avanti Ramrods & whatever maduro torpedos, coronas or toros I come across. There are very few flavored cigars that I favor, but I never get tired of the Bootlegged or the Ramrods. They are both subtle & strong.
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5 out of 5
Just what I wanted in a cigar, love the taste.
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5 out of 5
Great cigarrillos!!
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4 out of 5
Good enough for a quick smoke. Rolled a little loose.
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5 out of 5
Great cigar wool buy again
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5 out of 5
These are a great little smoke just what the doctor ordered. I dare you to give them a try, you won't be disappointed.
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5 out of 5
Great little cigars!
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5 out of 5
While I prefer the Bootlegged flavor, these are a close runner up. I usually have a box of each on hand for those times you just want a quickie.
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4 out of 5
Good inexpensive smoke
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3 out of 5
Flavorful, but loose and unraveling.
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5 out of 5
Very tasty. Smooth draw.
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4 out of 5
This is a lot of cigar for an inexpensive machine made cheroot! A nice mellow kick of rum-infused tobacco without being overly sweet. A good quick cheap smoke.
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4 out of 5
Easy pull with a light crisp flavor and is one of my favorite cheroots.
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5 out of 5
I love these. II have given them to a couple of friends and they always ask for more. Perfect for when I don’t have time for a full size cigar.
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5 out of 5
Great taste love the flavor
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5 out of 5
bootlegged the best,
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5 out of 5
good smoke price fair.
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4 out of 5
Good cigar for the money. The first one I smoked canoed and had problems with, the next three were excellent. Not as good as the Backwoods Black and Sweet but still a great smoke. Will buy again.
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