The eponymous Crossroads in the Crossroads District is the intersection of Brightshore's two largest roads, one which runs nearly the entire length of the settlement, through the Outer Gate into the wilds, and another which runs from the river to the walls of the keep. Ease of access from almost anywhere has made the Crossroads a perfect location for places like taverns, The Wink and Whistle Inn, and the Central Guard Post.

While the Market District might win the race for “busiest district,” it only holds that honor from sun up to sun down. Once the light fades and the shops close, the Crossroads is home to the town's nightlife, which is fairly tame, but perfectly adequate.

Brightshore's newest inn is a two-story building, festooned in colorful flags and streamers, and located on the southern corner of the Crossroads intersection. Compared to its competitor The Nicked Rock, the Wink and Whistle draws patrons looking for both dinner and a show, since the proprietor, a flamboyant, aging green dragonborn named Beryl, makes sure to have some sort of performance going on each night (the quality of which varies wildly). The first floor serves as the inn's common room, with a large fireplace, kitchen, bar, and a small stage to one side, and rooms are available for rent on the second floor.

It recently suffered a small fire during the production of the play “The Third Winter” and has just reopened after finishing repairs.

About two dozen volunteer town guards are actively working in Brightshore at any one time. Whilst on duty, when they are not patrolling the streets, wrangling criminals, or investigating infractions of the law, they can be found here. The building itself features holding cells for criminals, desks for the guards, an office for the Guard Captain, and a small training yard. In front of the building is a wood and glass display case, where tasks that the guards are unwilling or unable to do are posted. Guard Captain Redford Bolt, a gray-haired, dark-skinned human man in his mid-50s, runs the post with calculated precision, along with his assistants, Jamie Santangelo and Rafe Rialta.

In one of the least populated areas of the Crossroads District stands a crooked, slightly dilapidated building with a wooden sign above it that reads “Chateau of Wonderment.” A jar of variously sized eyeballs, a mummified hand of some sort, and a smoky mirror in an ornately carved frame are displayed in the curtained front window. The owner, a fez-wearing human man known only as Grumble Dan, is known for a having a keen interest in the weird and unexplained, and for a (non-refundable) fee will allow anyone to visit his fortune-teller. Grumble Dan also keeps a small museum of “cursed” art objects, jewelry, and other strange discoveries, which can be perused for another (non-refundable) fee.

Some of the exhibits that Grumble Dan has displayed in the Chateau include:

• a one-pound egg with a red shell
• a blank book whose pages never bear writing (with a coin slot for charcoal dispenser)
• a cherub-imp hybrid (looks suspiciously like an opossum with crow wings and goat horns attached to it)
• a “moonstone”—a white rock that Grumble Dan claims fell from the sky into the ruins; apparently turned Dan and several others into werewolves for a few months (but they were cured)