New Marlborough, Massachusetts
Meet your cheese at the source.
Hours From New York: 3.5
DAYTIME TEMP: 37 °
TYPE OF VACATION: Family Friendly
Some travel to see leaves turn; others brake for cheese. Start your cheese tour of the southern Berkshires with dinner in New Marlborough at Peter Platt’s recently renovated The Old Inn on the Green (from $205; 413-229-7924; oldinn.com): braised short ribs followed by a cheese plate that samples tastes from the farms you’ll be visiting. Stay there, or in Lenox at Stonover Farm (from $295; 413-637-9100; stonoverfarm.com), a B&B gone chic. Make sure to ask for proprietor Tom’s signature omelette at breakfast; he uses the herbed chèvre from the first stop of your day, Rawson Brook Farm in Monterey (413-528-2138). Here, Susan Sellew makes her much-lauded goat cheese in small batches. Pass through Gould Farm (413-528-1804), a rehabilitation facility whose residents work the land and turn out tasty mild Cheddar. Wheels of Michael Miller’s prize-winning Berkshire Blue are handmade with local Jersey milk at the dairy in Great Barrington (413-528-9529). Pace yourself, though: Plan on spending an hour with each monger, if you make an appointment, or, if doing a taste ’n’ run, 30 minutes at the most, and keep samples to no more than the size of your thumb. Next day, return to Great Barrington and stock up on the stuff you liked best at Rubiner’s Cheesemongers & Grocers—think Murray’s, New England–style (413-528-0488).
Port Henry, New York
Pull a dozen fish from a frozen lake.
Hours From New York: 4.5
DAYTIME TEMP: 36 °
TYPE OF VACATION: Male Bonding
The deep wintry silence, the mind-numbing action of tossing a tiny fishing rod on the ice and pulling up the line by hand every 60 seconds, the six-pack of beer before noon—no wonder locals bliss out on Lake Champlain, which borders New York and Vermont. It’s the mecca for this sport; it’s not difficult to snag over 40 pounds of perch, lake trout, and salmon in a day. Layer on plenty of thermal and goose down, pick up a $19 fishing license (if you’re a New York resident; out-of-staters pay $40) at the nearby Wal-Mart, then take a caboose or snowmobile a half-mile out on the lake. Poor Man Fishing Charter’s (518-942-7510) Thurman Cross has 27 heated shanties that fit up to six. He’ll drill the holes, provide the bait and rods, bring you lunch if the shanty’s propane stove proves cumbersome, and find your hotel room. A full day’s fishing costs $17.50 per person.
The Hamptons, New York
Have a cheap weekend on the South Fork.
Hours From New York: 2
DAYTIME TEMP: 41 °
TYPE OF VACATION: Romance
By early fall, you have all the sophistication of Manhattan’s playground (and the angels-may-descend-at-any-moment light), without the killing traffic, and at greatly reduced rates. You can have a $16 open-faced steak sandwich or a $14 lobster roll from the off-season lunch menu at the Palm in East Hampton (631-324-0411) and score a movie ticket with the $25 two-course prix fixe Wednesdays, Thursdays, and Sundays at Nick & Toni’s (631-324-3550). There are autumn prix fixe dinners everywhere: three courses for $30 at Della Femina (631-329-6666), $19.95 at Almond (631-537-8885) in Bridgehampton. Estia Cantina in Amagansett (631-267-6320) has weekend jazz where “dancing is encouraged.” Pick up a fresh apple pie at Round Swamp Farm. Hire a charter or book a spot on a working boat from Jack Passie in Montauk (631-668-5741), because the striped bass are running through November. Book at the clean, basic Enclave Inn (from $89; 631-537-5436; enclaveinn.com).