Muddy Cup - New Paltz, NY
Fair-trade coffeehouse located on Main St that offers open mic nights with acoustic artists, bands, and poets. Two floors with plenty of space and free board games.
50 Main - New Paltz, NY
Another fair-trade coffeehouse next to the Muddy Cup on Main St. Offers the same style of open mic nights and free music, but is more progressive-friendly and sponsors events in coordination with organizations like PETA.
The Chance Complex - Poughkeepsie, NY
Includes The Chance, The Loft, and the Platinum Lounge. Offers a wide variety of music, but it's always a good idea to check the schedule: there isn't a concert every night, plus the cost is occasionally quite high. Save The Chance for a band you really love!
The Cubbyhole - Poughkeepsie, NY
Located on Raymond Avenue near Vassar College, the Cubbyhole hosts open mic nights every Tuesday and sometimes also on Mondays and Thursdays. It also schedules bands to play for free. When you come on an open mic night, drink coupons are also given out.
Waryas Park - Poughkeepsie, NY
AKA "The Waterfront," Waryas often has jazz and big bands play for free. The park is also very child-friendly, as it has bathrooms, food, and a playground in addition to the beautiful scenery.
Spanky's, Mahoney's, Noah's Ark - Poughkeepsie, NY
The various bars in Poughkeepsie often schedule free music. Be careful of the age to get in, though, as some nights the age is 18, and the others, 21.
Oasis/Cab's - New Paltz, NY
Again, be careful of the age to enter. Cab's is always 18 to get in, while Oasis changes on a daily basis. Cab's usually features rock bands or 80's tributes, whereas Oasis is open to more experimental types of music.