Their year of sacrifice may officially be over, but Josh and Brent are still struggling with living apart as Brent runs the business in the village and Josh earns a paycheck in the city. The success of the Beekman 1802 brand results in a major life change for Farmer John, but not everyone on the farm is thrilled about it. Plus Polka Spot, the resident diva llama, has decided she no longer wants to be fenced in and her constant escapes are turning into a big problem. With an unruly llama, the financial strain of running a farm and the demands of growing the business ever present, Josh issues Brent a challenge that if accomplished, could make their dreams a reality.

Wanting to spend some time together away from work and the farm, Josh tries to convince Brent to take a vacation. Brent surprisingly agrees, but only because he has arranged for he and Josh to adopt Black Welsh sheep, not only for their farm, but a pair for Martha Stewart as well. Though it sounds more like a chore than a relaxing getaway, Josh reluctantly agrees to take a road trip from North Carolina to Martha's Bedford estate with four very noisy lambs in tow. But when they arrive in Brent's home state and Brent refuses to visit his nearby grandparents, Josh begins to worry that their relationship has caused Brent to become estranged from his family.

As their road trip up the east coast with Black Welsh Sheep continues, Brent and Josh make their way to Martha Stewart's Bedford estate to drop off her new lambs. The visit to Martha's pristine barn quickly inspires Brent to look into making some much-needed improvements to their 100-year-old structure back at the Beekman. While Josh is desperate to have a work-free weekend, Brent announces that the Beekman will host its own version of a barn raising with everyone in Sharon Springs welcome. In the true spirit of community, the villagers turn up for the event, but whether any work actually gets done by them, or by Josh, is all up to Brent and how hard he can crack the whip.

Brent continues to keep things moving with the Beekman business as he works to perfect the recipe for a spicy goat milk caramel sauce he wants to take to market. Meanwhile, Josh is still holding down his job in the city to finance the Beekman business, and he receives some unexpected news that could keep him from the farm more than ever before. But all those worries are pushed aside when Food & Wine magazine arrives at the Beekman for an elaborate photo shoot, and the boys have to focus on perfecting both the farm, and their outfits. When things return back to normal, Brent scores a tasting for his products with renowned chef Marcus Samuelsson, whose opinion on Brent's new caramel recipe could be the start of something great, or just send him back to the drawing board.

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After their modest success with last year's event, Brent is hard at work preparing for the upcoming 2nd Annual Harvest Festival. Knowing that the weekend ahead will be a stressful one, Brent and Josh make a pact not to argue and kick off the festivities with a sold out harvest dinner. But the festival quickly becomes more than what anyone in the village could have imagined when 5,000 visitors, including Rosie O'Donnell, descend on the tiny village and begin buying every wheel of cheese and bar of soap in stock.

Though Brent is reluctant to give up control, he agrees to let Josh head up development on the first ever Beekman 1802 cookbook. At the shop, Beekman employee Maria is keen to show Brent she can handle new responsibilities on her own as Brent heads into the city to prepare for a huge heirloom vegetable auction he's put together with Sotheby's. But when things don't go according to plan, with both the cookbook pitch and back at the Beekman shop, Brent begins to regret ever having given up control in the first place.

With Josh's parents, Jackie & Dave, arriving for a weeklong visit at the Beekman, Josh decides he'd like to see Brent have a closer relationship with Dave. Josh asks his mom to join him in Manhattan, in hopes that Brent's week with Dave will let him experience having a dad for the first time in a long time. At the farm, Dave and Brent embark on their bonding week complete with shotgun lessons and muskrat hunts. But whether Dave can really survive a week with the fussy Brent proves to be the biggest challenge of all.

After the success of the Harvest Festival, and still desperate to reach their million dollar goal, Brent decides to throw another festival in attempt to drive traffic into the village during the usually deserted harsh winter in Sharon Springs. The Victorian Festival is set in motion and the whole village gets into the act with Victorian-costumes, caroling, and carriage rides. When things wind down, Josh realizes there is one celebration they've been forgetting, and with Jason's help, they work to pull off what they hope will be surprise birthday party for Farmer John.

With the outcome of the million dollar challenge before them, Brent finds himself with a new opportunity. Los Angeles-based couple Susan & Yvonne buy a historic property in Sharon Springs to transform into a health care facility, and ask Brent to become their resident physician. Josh is thrilled at the prospect of Brent taking on a medical position and making a salary once again. But when Brent is reluctant to take any time away from the business, even though it would mean Josh could move to the farm full time, the situation between the two becomes tense.