The second-annual First Sip will offer deals on cocktail and mocktail specials, plus food pairings at around 30 restaurants, breweries, distilleries and liquor stores. Credit: John Herrick

When Colorado restaurants opened their doors again in spring 2021, Boulderites welcomed the return of their culinary favorites. For local foodie and entrepreneur Jessica Benjamin, the reopening posed a choice: sticking to her old standbys or venturing out to explore newcomers that had popped up during the pandemic. 

With her schedule tight, Benjamin came up with a plan: Why limit herself to a single venue when she could sample several places in one night? So she and her husband, Boulder City Councilmember Matt Benjamin, hopped from one restaurant to the next, enjoying a drink and a snack at each. “Committing to a multi-course dinner at one place felt so limiting,” Benjamin said.

The experience inspired her to create First Sip, a spin-off of her restaurant week event, First Bite. Instead of prix fixe, First Sip-goers order creative drinks á la carte. The idea is to help locals enjoy a night out without the constraints of a full-course dinner or the worry of exceeding their budgets — while being introduced to the local drink scene. 

“The beverage programs in this town are so spectacular that they deserve their own spotlight,” Benjamin said. 

The second-annual First Sip, taking place from April 26 to 30, offers some deals on cocktail and mocktail specials, plus food pairings at around 30 restaurants, breweries, distilleries and liquor stores around Boulder County. 

First Sip, as well as First Bite, aims to reimagine classic restaurant weeks by doing away with the classic prix-fixe menus and dining traditions. Restaurant week started in New York in the ‘90s to encourage summer visitors to try multi-course meals at fixed, bargain prices. 

“All traditional restaurant weeks still operate this way,” Benjamin said. Set menus require restaurants to offer experiences that don’t necessarily represent what they are, she added. For example, a casual brunch place might have to serve a fancy three-course meal. “The more traditional restaurant week model was forcing people into a box that wasn’t really themselves” and limiting creativity, she said. “They were being pushed into three courses.”

“We don’t have a set model” for how to participate, Benjamin said of First Sip and First Bite. “Your offerings should reflect who you are.” 

Revamping restaurant – and drink – week

Josh Dinar, founder of Ash’Kara, plus River and Woods, founded First Bite (the company and restaurant week event) with Kate Lacroix, who worked in local food marketing, in 2005. Benjamin took over First Bite in 2019 with five other women. Together, as Savor Productions, they remaking the restaurant week concept, she said, recently adding drink week.  

When Benjamin bought First Bite, she reached out to restaurants to hear what they thought about the organization’s event. 

Benjamin said the main feedback she got from owners was that the conventional restaurant week had become outdated. It also had become costly at a time when supply and labor costs are increasing. She explained that in previous First Bites, restaurants had to reduce their profit margins by so much, spending more on food and staffing, that they ended up losing money during that week.

“This was a time that was supposed to bring a little pulse to them,” she said.

Fifteen of last year’s 33 First Sip participants will return for the event’s second year. (According to Benjamin, those sitting the event out have new ownership, are closed, or “just didn’t have the bandwidth or feel it was right for them.”)

This year, offerings range from boozy specialty drinks to non-alcoholic milkshakes. At Dagabi Cucina, you’ll get a tapa for free when you buy a glass of tempranillo blanco wine for $11. Japango is offering a tasting of namazakes, or unpasteurized sakes. A flight of three is $17. 

Dry Storage, meanwhile, is offering a flight with iced kumquat-thyme espresso, raspberry vanilla matcha, and a hibiscus limeade for $13.

The Sink, to celebrate its 100-year anniversary this year, is offering $7.55 milkshakes, one with fruit loops and the other with maple, chocolate and bacon, plus limited-edition cocktails. 

Throughout First Sip, Basta will stick to restaurant week’s prix fixe tradition with a four-course cocktail tasting and food pairing for $55 a person.

Non-Boulder restaurants include 740 Front in Louisville and Ghost Box Pizza in Lafayette. 

While none of these events are ticketed, Benjamin recommends making a reservation, since many restaurants are still understaffed from the pandemic. Some restaurants will offer their own ticketed events on their websites or at the restaurant. On April 30, The Hungry Toad, for instance, is selling $25 tickets for a scotch tasting.

During the month of April, customers can nominate someone for the Badass Bartender Award from any participating First Sip restaurant. The winner receives $250 cash and a prize pack. 

“Sometimes the best part of going out for a drink is not necessarily the drink itself, but the bartender,” Benjamin said. “These drinks don’t pour themselves.”

First Sip goes from April 26 to 30 You can find a list of deals here

Jessica Mordacq is a contributor to Boulder Reporting Lab focused on local food and drink coverage. Originally from the Chicago suburbs, she graduated from Northwestern University’s Medill School of Journalism and has previously written for various trade and lifestyle magazines. Email:

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