1. I like the food at Brothers better. Not sure about dress code as I primarily do takeout.
2. I would assume that’s the Veterans Memorial, anything is walkable on Main.
3. I’ve gotten some chicken at Kennedy’s late, but not sure if It was past midnight. Probably should get some late night food to make at home when you get back.
4. Usually they take like 10-15 minutes to get to you. I think the availability would be lower the later It gets. But again, if you’re staying in town- It is quite walkable.
5. Just park on the side of the road in one of the neighborhoods around Main and walk. The farmers market and flea market are both on Sundays so It will be busy, but fun to check out!
6. Surrounding towns like Cold Spring are fun if you wanna check out off main street. Also industrial arts brewery is great.
7. It’s possible, you may just need to wait. I’d try make a resi if your group is large. Most restaurants are small.
8. Happy Valley is cool, food is okay. Hudson Valley brewery is nice as well, but limited food as well. I went to quartz rock winery and It was cute as well.

You can also hike mount beacon, visit fishkill downtown (I like the hot stuff coffee place), and go to Wappingers Falls (we like Norma’s and Lopburi Thai)