Eventually, when you get around to Shire adventures...

[Dedicemancometh]

I just wanted to put in my two-cents for a more fun and "children's story" set of adventures for the Shire that could segway into the more serious tonality of Bree and further East and South.

Of course, you can overdo anything, but some fun and puns with low-stakes adventures is sometimes just what the doctor recommended.

Eventually, adventuring parties will deal with some of the other (sombre/sober) campaigns you've published. But it is nice to start out innocent.

[Glorelendil]

But with lots of hints and foreshadowing of darker things to come. In my opinion.

[Otaku-sempai]

Definitely some downtime activities in the Shire should include cultural festivities for various times of the year including local fairs and the Free Fair. Suggestions could be made for games and contests and how to adjudicate them. The Hobbit lists several such games that are commonplace in the Shire.

Optional rules for gambling can be found on pages 130 & 131 of Xanathar's Guide to Everything for D&D 5e. For that matter, carousing is similarly covered on pages 126 to 128.

Inns and taverns of the Shire:
• The Green Dragon, an inn on the Hobbiton side of Bywater.
• The Ivy Bush, a modest inn located on the Bywater road in Hobbiton.
• The Golden Perch, an inn in Stock, said to have the best beer in Eastfarthing.
• The Bridge Inn at the west end of the Brandywine Bridge.
• The Floating Log, a popular inn in Frogmorton.
• The All-welcome Inn on the Hobbiton side of Frogmorton.
• The Rabbit Hole, a tavern in Greenfields (my personal contribution).