Fresh off raking in a slew of “best of” awards from the Colorado Springs Independent — including wins in categories like Mixed Drinks and Place to Meet Singles — the Wobbly Olive has followed up its new fall food menu with an massive overhaul of their cocktails. With 46 new drinks appearing on the menu, a noticeable facelift offers up tons of new imbibing options. “We want to reinvent every season,” says co-owner Sean Fitzgerald, half of the husband-wife team with Inez Fitzgerald who flipped the script on eating and drinking on Powers Boulevard. “We’re ambitious.”

“One thing that we changed was the first page of our cocktail menu.  Every time we do a revamp we try and put something that as bartenders we find to be humorous,” Sean tells the Food Report in a recent sit-down. “This is the page we use to show our personality, our quirks. In this case: quotes, people talking about alcohol.”

The Wobbly Olive took home gold for neighborhood restaurant-east, upscale bar, neighborhood bar-east, mixed drinks, place to meet singles.

Among Fitzgerald’s favorite is this one commonly attributed to Frank Sinatra: “I feel sorry for people who don’t drink alcohol. When they wake up in the morning, that’s as good as they’re going to feel all day.”


“A lot of the naming of our drinks comes from ’80s rock songs or current television shows we’re watching,” says Fitzgerald.

A spooky October-appropriate show prompted the Penny Dreadful: Ford gin, house-made mission fig cordial, aged balsamic vinegar, egg white, fresh lemon, and honey with cracked cardamom seeds perfectly placed on top of a frothy veil created from a reverse dry shake.   “I recommend having this after the appetizer and before the entrée.  It just refreshes and cleans everything.”

Penny Dreadful, you slay me
Line up the cardamom

We tried other notable newbies like the Jump the Shark, with Redemption rye, orange curaçao liqueur, a dash of sherry, and vanilla-orange bitters.  It tasted like warm vanilla beans laced with spice, and featured Valencia organge presented in a thin crystal, open-faced glass.

Jump the Shark– a good Happy Days reference

Next came God is a DJ. Made with Anejo tequila, homemade strawberry cordial, jalapeño-infused agave syrup and fresh lime juice in charged water, it’s proof that sometimes it’s hard to say goodbye to the warmer months.

Who knew the Wobbly loved Pink so much

No worries there, though, because Fitzgerald is offering up a tropical Christmas with a new section called Endless Summer.  “I wanted to put some classic, old school, tiki drinks on the menu,” he says.  We tried the Beachcomber: Cana Brava rum, Luxardo Maraschino Liqueur, triple sec, lime juice and a bit of baker’s sugar.  Or another: The Painkiller — like a mellow, coconut-forward piña colada on the rocks — featuring Myer’s Jamaican rum, cream of coconut, pineapple and orange juice with nutmeg.

Beachcomber gettin’ in done
Dull your problems with coconut year-round

“We like to have a section of just seasonal drinks, where things are available only for a short period of time,” says Fitzgerald.  You can sample this fall staple made with homemade pumpkin pie purée and sweet vanilla cream through November.

Other seasonal provisions include a Wobbly Hot Toddy, which Fitzgerald says “isn’t traditional — it’s something my mother used to make for me when I was sick. She used to call it the Dr. Feel Good.”  It features Jameson whiskey; limoncello; a syrup made up of star anise, cinnamon, clove, and angelica root; all set in an orange-spice white tea, with lemon for a citrusy throat coat.

Hot Toddy for those cold nights that are coming

“A lot of places are scared to try and do egg nog, especially to-order, because it’s a difficult drink.  We’ve been able to perfect this just with our shaking technique.  You want it to completely emulsify,” says Fitzgerald. Thus, Apple Pie Nog is a creamy, delightful blend of Crown vanilla, and a homemade cordial of Diva apples, cinnamon syrup, a raw egg, heavy cream and grated nutmeg. (Toss that carton of nog away, for shame.)

Wobbly’s Oink-Fashioned is a satisfying deviation from the classic. This bourbon is fat-washed with pork belly, combined with smoky pipe tobacco bitters and coupled with a quarter-ounce of maple syrup. The result is a cherry hickory dream, typically with a bacon skewer to stir it all up.

The Oink-Fashioned: like drinking bacon, in a good way.
Crushing on this drink

The Tequila Mockingbird, created by Inez, features Sombra mezcal, an artichoke liqueur, Angostura Bitters, and grenadine with POM and lime juices to balance out the intensity.  The tart pomegranate makes this drink layered and approachable.

Mezcal-fan and co-owner Inez makes a beautiful beverage with the Tequila Mockingbird.

Inspired by how he grew up, Fitzgerald wants to change the expectations around the drinking and dining experience. Sipping cocktails can be an something that lasts hours, prepping the palate for what’s next. That appetite for nostalgia is seen with Wobbly’s long drink called the Cranberry Quill: an aperitif to have before the meal, sipped slowly like sherry.  It’s served in a small, delicate glass, offering house cranberry gin, Lillet Blanc, and simple syrup. A sprig of rosemary resembles the plume on an old quill pen.  It’s refreshing and low in alcohol, a lovely introduction to the evening.

Sean Fitzgerald with his Cranberry Quill.

“I’m starting to gravitate towards this. I want to bring back the art of conversation, at least to my establishment,” says Fitzgerald, noting his newly anointed role as brand ambassador for Colorado Springs’ Lee Spirits Co. “I have one TV and I’m about 30 minutes away from getting rid of it.  We [want] people to talk and get to know each other — comradery and fellowship.”


Coming up, the Wobbly Olive is hosting its third annual Halloween party, called Neon Fright Night, on Monday, October 31.  Tickets get you unlimited cocktails, endless buffet, a costume contest and scary movies.  For questions or more information email: info@wobblyolive or find details on Facebook here.

[Images: Dionne Roberts]