Cash & Olive’s Pub

by | Mar 1, 2024 | 0 comments

Driving to Cambridge from Madison you get just a taste of fresh air before coming into the historic Main Street of downtown Cambridge. With a population under 2,000 this small village grew around vacation tourism from Chicago but is an easy drive for those living in surrounding population centers such as Watertown, Fort Atkinson, Edgerton, Lake Mills, Jefferson, and Whitewater. Just when you think you may have driven a bit too far, you will see the rainbow flag that marks your destination.

The building is more than 100 years old and was a postal stop in a former life. Both owners agree it’s probably haunted, but they fell in love with the location despite seeing dozens of others throughout the years. The property encompasses two acres and backs up to a golf course, which offers diners a view of a broad greenscape. It also offers living space above, meaning that they were able to cut out the commute. It has its own well, which has proved vital in a municipal area where water costs have recently increased rapidly.

The Millie’s breakfast menu is now available as a drive thru service (7 days a week 6:00 a.m.–11:00 a.m.). Typical coffee items are available along with a couple of unusual items: A Breakfast Baleada and Avocado Crumpet. Decked in green and gold inside, you will know that you are firmly in Packers territory here, but there is a stylishness and flair to the comfortable bar stools and checkered decor that give the front bar a sodashop vibe. They originally opened the bar and dining room under the location’s previous name, The Sports Page, but have now rebranded as Cash & Olive’s Pub—named in honor of their dogs.

They have revamped the menu but kept the hand rolled pizza that was a favorite with locals—except on Supper Club nights (1st Fridays) when the pizza becomes unavailable in favor of relish trays, steak dinners, classic fish fry, shrimp dinners, and a salad bar. Each day of the week, there is also an additional menu item available with most items made from scratch in-house where they hand-bread items, smoke meats, and corn their own beef. Starting in April, they hope to host a farmers’ market Thursdays that will give them access to more locally sourced ingredients. For the odd item now they run to the local Piggly Wiggly.

Courtney laughs about how you run into absolutely everyone while you are at The Pig looking for something like shallots—which a small regional grocer might not even carry—and you can’t judge a book by its cover. The most unlikely looking individuals have turned out to be part of the community, or allies, but there are challenges to developing in a rural area. Their rainbow flag was stolen several times before the culprits gave up, which was unsettling. It has also been difficult expanding their offerings in a village that just isn’t accustomed to doing much permitting. Things like pouring a new patio and offering outdoor gatherings can be slow-going with local officials that need time to familiarize themselves with the relevant ordinance. Recently area communities also withdrew from joint agreements for public safety leaving the future of those services unclear.

Courtney describes the businesses as her toddling children and absolutely has the no-nonsense parental vibe that can command a kitchen or bar. While I enjoyed my mocha latte she seemed alert to every coming and going around the building and shooed a lost utility contractor away while Jen checked in with the morning staff (who all seemed happy to be at work). The pair seems prepared to endure through any changes and rely on themselves and their supporters to continue building and hosting organizations like Lesbian Pop-up Bar, New Beginnings Shitzu Rescue (with a potential outdoor Yappy Hour in the works), and Valley View Recreation Club (locally known for their Annual Nude Car Show).

For larger events they bring in private security. That was the case for last year’s Pride Storm event which they hope to continue holding annually the first Saturday of October. They have space to park 60 cars, host 27 vendors, and erect a stage—all on private property (no protesters allowed). For those who want to visit sooner, check their website for specials and information on their upcoming events, including the Divas & Dives drag bus tour on May 4. 

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