Dan wants the city of Wessex to go green with its garbage. He solves the garbage problem by striking a deal with the neighbouring city of Glenbridge, only to be foiled by their crafty mayor and her goat. The Mayor's new policy has everyone down in the dump.

Dan gets on the wrong side of the Chief of Police when he tries to stop the upcoming purchase of 50 Speedoos (personal mobility devices). Although the Chief appears to accept Dan's decision, bad luck suddenly falls upon Dan and his friends. Mike's moustache finally comes in handy when he bonds with the boys in blue.

Dan jeopardizes his popularity when he proposes a property tax hike. A council meeting has him running late for his stint as a celebrity judge at a spelling bee. His tardiness doesn't go unnoticed and Dan forgets to go "off the record" with an overzealous, student journalist, resulting in a larger story in the Wessex Herald highlighting Dan's extraordinary spelling skills. Meanwhile, Mike finds himself upgrading on the girlfriend front.

Dan hosts his first annual Mayors' Conference only to learn that hanging out with the mayors isn't much different than being back in high school. Now that Claire and Dan are a committed couple, she needs to move all her stuff out of storage and since Dan is too busy with the conference, Claire turns to Jeff and Mike for help. Suddenly a competition develops when they each work hard to ensure that the other isn't available.

Dan plans to open new bike lanes in Wessex, but first he will need a new bike, a point of contention with Claire. Mike wants Dan to share the bike lane with roller-bladers, but is there enough room? Over at Fern's, Fern has let their liquor license lapse, an oversight he doesn't share with Jeff.

Dan wants Wessex to be featured on the upcoming Art Trail, but Wessex doesn't have much in the way of art. Dan remedies this by commissioning a sculpture. Fern's gets a VLT (video lottery terminal) machine, which turns out to be quite addictive. Claire is bidding for a new job – it just happens to be an anti-gambling campaign.

Everyone wants a piece of the Mayor. Dan feels obligated to take on a speaking engagement for Fern but doesn't clear it first with his Chief of Staff, landing him on stage at a pot rally. Claire's parents are divorcing and Mike is devastated. When he tries to intervene, he ends up in a completely inappropriate and unintended dating situation.

As the new Mayor of Wessex, Dan finds himself having to attend a variety of events from pig roasts to pancake breakfasts. With Claire on his arm, he is unsure whether she is a political asset or liability. Alan already has his mind made up and imposes himself as the Mayor's handler by keeping Claire occupied. Mike tries to insinuate himself into a budding friendship with Jeff by pointing out that Mayor Dan doesn’t have much time for his old pal Jeff anymore.

Dan takes a trip down memory lane when he visits his high school workplace, Old Fort Wessex. Sadly, the fort has seen better days, so Dan commits to his old boss, the Fort's General, that he will do his best to turn things around. Claire plans to lure Japanese businessmen to Wessex and inadvertently creates a solution for the cash-strapped Fort. Meanwhile Jeff tells Fern that there are tunnels under the bar, and all the routes lead to Old Fort Wessex.

Dan is mentoring a young "Mayor for the Day" and the kid is giving him a run for his money by undermining Dan's credibility with the media and City Council. Meanwhile, it's time for the annual Best of Wessex Awards, and Claire is so busy looking busy, she doesn't even realize she's in the running. Now that Jeff owns Fern's he thinks he has a stab at Best Bar Award, but Fern knows all too well - awards come at a price.

The Mayor's relationship with Claire has him providing full disclosure to the questionably ethical Ethics Commissioner. Jeff attempts to out-customer service Fern and winds up behind bars. His one call goes directly to City Hall hoping his buddy the Mayor can make things right.

Dan is about to open the annual Porktoberfest by taking a bite of the Golden Bratwurst – a task made difficult by his vegetarian status. Jeff is confused by Dan's seemingly bi-dietary lifestyle. After a radio spot, Wessegonians start to question their own dietary choices, leaving a lot of uneaten pork in Wessex. Mike takes his role of Hambassador so seriously it has him donning lederhosen and eating more than his share of pork products.