There are undoubtedly tons of trends in the cocktail and alcohol space that come and go, but bourbon is that classic staple that will seemingly never go out of style. Bourbon is, at its core, the American version of whiskey that has been a reliable liquor on bar shelves since at least the 1800s (via American Whiskey Trail). According to Bourbon Country, the spirit stands out from general whiskey because of its mash bill — bourbon is almost always majorly comprised of corn, resulting in its sweet and smooth flavor.

There are plenty of mainstream bourbon brands, like Knob Creek or Evan Williams, that likely look familiar even to someone who never usually touches brown liquor, let alone sips it straight up. As with most other categories of spirits on the market, there are also a few lesser-known bottles of bourbon worth trying out at least once. Whether it’s a limited release or a bottle that generally isn’t shown enough love, we’ve rounded up a few underrated bottles of bourbon to try before the end of 2022. There are options perfect for cocktails like a Hot Toddy or a Kentucky mule, but all are also great for sipping straight up and exploring the intricacies of every release. It’s a good excuse to enjoy a drink in the name of expanding your palate, as every bourbon enthusiasts knows is very important.

Five Trail Flagship Blend

Five Trail Flagship Blend is technically a blended whiskey, but only 8% of the blend is made of single malt whiskey while the rest contains various aged straight bourbons, so we let it slide. The entire blend has a Colorado spin as it’s proofed with water from the Rocky Mountains, making for even more of a distinct flavor. Five Trail features two bourbons aged for four years apiece, one containing rye and one not, and one 12-year-old Kentucky bourbon. The result is a complex blend of warm flavors like caramel, ginger, wood, and baking spices that envelopes your mouth in the best way imaginable.

This $60 bottle is one you’ll want to enjoy straight on the rocks, or at the very least in an old fashioned with the best ingredients (via Total Wine). "It’s more than just a delicious drink, it’s an experience," writes one fan of Five Trail Flagship Blend in a comment on the brand’s Instagram page.

Grand Teton Private Stock Straight Bourbon

Grand Teton Distillery makes a lot of spirits that are very much worth shelling out the cash for, but their Private Stock Straight Bourbon is the only one to hold the title of the oldest whiskey from a distillery Idaho. The distillery ages its bourbon for 8 years in single barrels, so each bottle is complex and distinct in flavor. The mash bill also contains 21% rye, meaning there are flavors of bitter chocolate and light pepper present among the woody and vanilla notes.

In general, this a bourbon that channels the flavors and experience of homemade campfire s’mores in the best way. It’s up to you to decide whether or not that experience is worth the $80 price tag. "Flavorful and smooth. I’m glad I got a chance to taste it when my wife and I toured your distillery," one fan of the bottle wrote on Grand Teton’s Facebook page.

Baker’s Bourbon

Baker’s Bourbon was created to honor longtime Jim Beam distiller Baker Beam, who was literally born and raised on the distillery grounds in Clermont, Kentucky (via Beam Distilling). Considering its a single barrel bourbon, no two bottles are exactly alike (via Paste Magazine). It’s taken up a notch when you consider that not only is each barrel different, but the bourbon is aged in one of four locations, which also impacts the flavor. Each bottle is aged for at least seven years to develop those deep caramel and vanilla notes, with a strong chocolate flavor present.

An added bonus is that each bottle of Baker’s has a serial number so you can track the journey your bottle went on before making its way into your glass. Furthermore, every bottle has a collectable cap to make purchasing one for yourself even more of a treat. "Very smooth sip for a 107-proof. The flavor is mild and well relaxed. Definitely a top one for me so far," one Flaviar user wrote in a review. A bottle of Baker’s sells for about $60 on Total Wine as of October 2022.

Samuel Maverick Private Reserve Straight Bourbon Whiskey

Samuel Maverick Whiskey is a proud institution of San Antonio, Texas, with the distillery having a prized location right by the historic Alamo building. The brand honors the practices of traditional American bourbon but with an added Texas twist with its latest release – Samuel Maverick Private Reserve Straight Bourbon Whiskey. It’s a small-batch limited release that is an ode to the brand’s namesake — it was made and distilled on the site of prominent Texas politician Samuel Maverick’s original home from the 1800s.

Maverick Distillery only used seven barrels of their 4-year-old reserve to make this particular bourbon, so it’s a pretty exclusive sip (via BevNet). The 90-proof bottle sells for $75. The flavor features the warm and slightly sweet notes you’d expect from a bourbon, like caramel, chocolate, and vanilla, but with a twist that resembles smoky Texas barbecue. "It’s amazing," one fan of the release wrote on Maverick Distilling’s Facebook page.

Widow Jane 10 Year Bourbon

A bourbon from Brooklyn, New York? It can be done, and done well, as evident with Widow Jane 10 Year Bourbon. The brand uses a blend of straight bourbons aged for a decade. The distillers pay attention to detail by making this bourbon in five-barrel batches and proofing it with water from the Rosendale Mines in New York. The flavor of Widow Jane 10 Year resembles that of a well-balanced old fashioned. There are fruit notes like orange and cherry mixed with the warm flavors of vanilla and maple. It also has a pleasant spicy finish that adds even more depth, meaning that you’ll want to sip this one slowly and straight up to appreciate everything that’s going on inside. "I got to try a sampling of it, then choose to buy the bottle," one Flaviar user wrote in a review of the bottle, adding, "It’s probably one of my favorites and it reminds me of those orange chocolate candies."

Legent Bourbon

Legent Bourbon bottle on table

Legent Bourbon feels like a perfect marriage between Kentucky bourbon and Japanese whiskey, thanks to the collaboration between Fred Noe and Shinji Fukuyo. The standout aspect of Legent is that some of the bourbon in the blend is finished in red wine and sherry casks to develop a deep flavor of fruit and aged wood. It’s all meticulously blended together, creating a bottle that is layered with flavors and perfectly balanced. It has slight peppery spice that meets rich flavors of dark chocolate covered cherries.

This bourbon is fairly priced at just over $40 a bottle on Drizly as of October 2022, so it’s an easy way to treat yourself to something new to expand your bourbon palate. "Fantastic flavours, great blending…only problem is that it is not a bourbon to mix with cola….only way to enjoy it is straight up," one Master of Malt user wrote in a review of Legent.

Night Sweats Bonded Straight Bourbon

Night Sweats Bonded Straight Bourbon

Another recent release as of October 2022 comes from The Block Distilling Company, and it’s worth getting your hands on while you can. If you need more convincing, the brand is only releasing 700 bottles and once it’s gone, it’s gone. The distillery’s Night Sweats straight bourbon whiskey is bottled in bond, meaning it is aged for a minimum of four years and bottled at 100-proof, among other qualifications (via Whiskey Raiders). The mash bill includes a blend of millet, malted barley, and a combination of yellow, blue, and red corn. Most of the grain comes from a farm associated with The Block’s distilling practicing, meaning they have even more insight into what exactly goes into their product. The result is a bourbon that is sweet like its honey color thanks to all of the corn, with other earthy elements to make it feel more robust.

The bottles sell for $90 each, but $10 from every sale goes to support The Marigold Project, which supports community and nonprofit organizations aiding in issues of economic, racial, and social justice. It’s a limited release worthy of splurging that also benefits a good cause.

I.W. Harper 15-Year-Old Kentucky Straight Bourbon

I.W. Harper Bourbon bottle

Another sweet bourbon that is a bit lighter for those who are still exploring the intricacies of bourbon is I.W. Harper’s 15-Year-Old Kentucky Straight Bourbon. The age adds plenty of depth to this 86-proof bourbon, but it isn’t as boozy as some other options on the list, which gives it a lighter mouthfeel. It’s got a good balance, is complex without being too overwhelming, and also shows how age can really transform a corn-heavy bourbon into something unique.

Some reviews on Flaviar suggest that you definitely want to let this bourbon breathe a bit so it can really develop its best flavors. "This bourbon in particular is a new favorite, and makes drinking any of my other bourbons much more difficult. This stuff is buttery and fruity but not overwhelmingly so, loads of flavor, and the finish is long and outstanding with very little burn," one review reads.

Pinhook 2022 Flagship Bourbon

Pinhook Flagship Bourbon bottles

Pinhook Bourbon is as Kentucky as it gets. Aside from producing some must-try bottles of bourbon, the brand also pairs each expression with a racing horse to further celebrate the state’s culture. Pinhook Flagship Bourbon is one bottle worthy of a permanent spot on your bar shelf, right beside bigger names like Bulleit and Maker’s Mark.

The 2022 expression contains a corn-heavy mash bill, paired with a bit of rye and malted barley for added spice and unexpected fruity flavors. The 100-proof bottle is aged for a minimum of three years, and it’s paired with a horse named Bourbondini. The flavor is deep and almost resembles that of a pie — it’s heavy with notes of peaches, honey, clove, and cinnamon. Plus, for $32 a bottle at Total Wine, there’s no excuse not to try it at least once. "Tried on recommendation requesting smooth, good tasting bourbon. Did not disappoint! Ordering three more today," one customer wrote in a review.

Pursuit United Bourbon

Pursuit United Bourbon bottle

If bourbons that tend to be on the sweeter side aren’t your thing, it may be worth it to explore bottles with mash bills that contain other grains, like wheat or rye, that add spicy and herbal elements to round out the flavor. One bottle that fits the bill is Pursuit United Bourbon, a 108-proof release made from a blend of bourbons that contain various levels of corn, rye, malted barley, and red winter wheat. The brand uses bourbon distilled in three different states — Kentucky, Tennessee, and New York — to truly make a release like no other.

It’s priced a bit higher at $65 a bottle, but it’s one of those slow sippers worth taking the time to explore the various notes and flavors going on inside. "This is one of the best bourbons I’ve ever had! What an incredible blend, nicely done," one Binny’s Beverage Depot customer wrote in a review of Pursuit United Bourbon.

Rebel 10-Year Single Barrel Bourbon

Rebel Bourbon bottle and glass

Lux Row Distillers’ line of Rebel Bourbon is another great brand to try if you want to explore the way slight adjustments to bourbon, like age or barrel proof, can have a major impact on the finished result. One standout from the line is Rebel’s 10-Year Single Barrel Bourbon. The 100-proof bourbon is aged for a decade in the standard charred oak barrels, but the bottle is a demonstration of how quality execution makes a big difference.

The notes in this one are what you might expect from a mash bill comprising of corn, wheat, and malted barley — oak, spice, and caramelized sweetness. There’s also a lot of orange zest coming through. While these may sound like standard bourbon flavors, the bottle proves that basic is anything but boring. "Solid pour! Not too sweet or spicy. A nice oak and fruit nose. The finish has some caramel and nuts in it. I will display this bottle proudly," one Flaviar user wrote in a review. Rebel 10-Year Single Barrel Bourbon sells for about $80 on Total Wine as of October 2022, so it’s a bit on the higher end of bottle prices.

Breckenridge Bourbon

pouring Breckenridge Bourbon into glass

Breckenridge Bourbon not only stands out because it helms from Colorado, rather than Kentucky or Tennessee, but also because it is a peppery, high-rye spirit. This 86-proof bottle has a deep golden amber color and a rich brown sugar and honey flavor to match. Breckenridge Distillery ages its bourbon for a minimum of three years to develop those deep woody flavors that compliment other warm notes of vanilla and caramel.

Breckenridge Bourbon is a relatively budget-friendly bottle that sells for $45 on Drizly as of October 2022, and reviews from customers who have purchased it declare that it’s an underrated gem that they would be willing to pay much more for. "This stuff ruined all my other bourbons. Absolutely the best," one customer review of Breckenridge Bourbon reads. And if you want to up the ante, the distillery also has a single barrel bourbon aged up to 10 years that’s even more of a rollercoaster ride of deliciousness for your taste buds.

Cedar Ridge Iowa Straight Bourbon Whiskey

Cedar Ridge Whiskey proves that Iowa might truly give Kentucky a run for its money in the bourbon department. Okay maybe we won’t go that far, but the brand’s Iowa Straight Bourbon Whiskey is one of the most underrated bottles at the liquor store. Cedar Ridge bourbon is freakishly smooth. The 86-proof bottle is predominantly comprised of Iowa corn, with a little rye and malted barley for good measure. The sweet corn flavor remains intact through the finish of this bourbon, with notes of toffee, vanilla, and caramel corn shining through.

It’s also a bottle that only goes for $40 on Drizly as of November 2022, and most satisfied customers seem surprised that the distillery doesn’t charge more for this must-try bourbon whiskey. "It was absolutely the smoothest bourbon I have had, but not lacking in complexity. The Iowa corn is evident in its sweetness, but caramel and grassy notes come through nicely," one Total Wine customer wrote in a review of the bottle.

Redwood Empire Pipe Dream

Another unexpected knockout bourbon that doesn’t call Kentucky home is Pipe Dream Bourbon from Redwood Empire Whiskey in Sonoma County, California. The first bourbon from the brand is named after the 14th tallest tree on Earth, called the Pipe Dream Tree in Humboldt Redwoods State Park. The tree is a whopping 367 feet tall and more than 1,300 years old, and its age and earthy qualities are represented in its namesake bourbon. The corn-heavy spirit features a blend aged anywhere from four to 12 years. It has the slight sweetness you’d expect, but not as much as some of the other options on this list.

Pipe Dream bourbon shows its age in a good way, thanks to its complexity, and the woody notes remind you of the brand’s mission. For every bottle sold, Redwood Empire plants a tree, so you can actually feel like you’re doing something good by treating yourself to this bourbon. It’s also very reasonably priced at $40 a bottle on Total Wine. "I was pretty wowed with this one," one customer wrote in a review of the bottle, adding, "I would compare it favorably with Eagle Rare. Lots of flavor for 90-proof and the price point."