Kutsher's Country Club
Chicago, Illinois (2 hours from NYC)
Chicago boasts two of summer's biggest music tickets—the behemoth Lollapalooza(lollapalooza.com; Aug 6--8; three-day pass $215) and Pitchfork Music Festival (Union Park, 1501 W Randolph St, pitchforkmusicfestival.com; July 16--18; $40 per day). Festival passes are the most painful investment, but Chicago has plenty of budget-friendly hideouts where you can kill time when you're not rocking out in the fields. Nostalgic types will appreciate Lollapalooza headliners Soundgarden, Green Day and the Strokes, while the omnipresent Lady Gaga returns to the fest as well (she first played in 2007). There are tons of recent fan favorites, too, including Arcade Fire, Frightened Rabbit and MGMT. For those with more indie tastes, Pitchfork's lineup stars Pavement, LCD Soundsystem, Modest Mouse, Surfer Blood, Titus Andronicus and more.
In between sets, check out the Rocking Horse (2535 N Milwaukee Ave; 773-486-0011,rockinghorsechicago.com) for a cold beer and classic American fare. Saint Alfred (1531 N Milwaukee Ave; 773-486-7159, stalfred.com) is a required stop for sneaker fiends—you'll need a new pair to keep your dogs from barking during those long hours pressed up against a stage. "They always have the flyest selection of gear and kicks," says local music producer Maker. The store carries everything from limited-edition Nikes and Vans to New York brands Alife and Mishka. Just across the street isReckless Records (1532 N Milwaukee Ave; 773-235-3727, reckless.com), the rumored inspiration for the film version of High Fidelity, where audiophiles can dig through old and new stacks of LPs and CDs. And if it's class you're after, Murasaki Lounge (211 E Ontario St; 312-266-2280,murasakichicago.com) is your oasis, featuring a wide selection of sake, boutique cocktails (try the popular coconut-lemongrass Sake-Lada, $12) and appetizers, plus a private karaoke room. It's also within walking distance of Lollapalooza headquarters at Grant Park.
Don't let the name scare you: The House of Two Urns (1239 N Greenview Ave; 773-235-1408,twourns.com; $89--159) is a cheap, convenient alternative to boutique hotels in the downtown Loop area, and offers a free breakfast from 7 to 10am, as well as vegan-friendly meals. It's a short walk to Division Street shops, cafs and restaurants, and one stop on the Blue Line from the barhopping neighborhood Wicker Park.
By train: Portland, Maine (4 hours from NYC)
Skip the scorching Coachella desert for the psychedelic wilds of Maine, and pitch a tent at the inaugural edition of the Nateva Music and Camping festival (natevafestival.com; July 2--4; three-day pass with camping $249, without camping $229, Sunday pass only $89). Sleeping in the Oxford Fairgrounds affords you the benefits of free Wi-Fi and computer- and cell-phone-charging stations, so you can update your Twitter and Tumblr accounts all weekend long with reviews of the Flaming Lips, moe., the Grateful Dead's Phil Lesh and Bob Weir, George Clinton and Parliament-Funkadelic, and Ghostland Observatory.
If you'd rather not cook out, take the advice of New York transplant Bryan Bruchman: Hot Suppa (703 Congress St; 207-871-5005, hotsuppa.com) is the place to go for brunch. Their corned-beef hash ($8.95) "was good enough to convince me to move to Portland from Brooklyn and not starve," says Bruchman, who runs Portland music blog Hilly Town and decamped from New York City in 2008. You can also cruise for some late-night eats at Irish pub The Snug (223 Congress St; 207-772-6839,thesnugpub.com). "They they have Brooklyn Lager," he says. It costs only $4 in Portland, so you'll feel right at home, minus the price tag.
If the idea of sleeping outdoors gives you hives, check in to the picturesque Chadwick B&B (140 Chadwick St; 207-774-5141, thechadwick.com; during summer months $160--$185). Innkeeper Buddy Marcum is also a flight attendant, and he lives by the motto "taking care of guests from the ground up." After breakfast (try the eggs Benedict or stuffed peach French toast), ask Marcum to set you up with a boat tour just a few minutes away at the harbor.
By car: Monticello, New York (2 hours from NYC)
Kutsher's Country Club (Kutsher Rd, Quickway Exit 105B; 845-794-6000, kutshers.com) in Monticello, New York, is the stuff of legend, established in 1907 as one of the classic borscht belt resorts that attract big-name musicians, comedians and athletes. It's no surprise that All Tomorrow's Parties (atpfestival.com) organizers chose the resort as home base for the U.S. branch of its music festival, which began in the U.K. and expanded stateside in 2008. It's become something of a summer camp for acult rock & roll fans, and this year's fest (Sept 3--5) will be guest-curated by filmmaker Jim Jarmusch, with performances by the Brian Jonestown Massacre, Fucked Up, Black Angels and others. Offstage, some musicians play impromptu sets in their hotel rooms, and there's plenty to do between the cinema room, pool, lake and card room (you never know who your dealer will be). If your bunkmate is driving you crazy and you need to escape camp for a while, nearby Blue Horizon Diner(4445 Rte 42 N, 845-796-2210) specializes in Greek and Italian dishes like panini and gyros (dinner $8.95 and up).
Kutsher's is sold out, but rooms at the similarly kitschy resort Raleigh (12 Heiden Rd, South Fallsburg, NY; 800-838-3006; three nights, four per room, $710) are still available. There's a free shuttle between the two locations, so you can catch all the action.