Where to Stay
Book a room at the two-story Castle Rock Country Inn (39339 Cabot Trail, Ingonish; 888/884-7625; ingonish.com/castlerock; doubles from $140) for the vertiginous view: the 15-room property sits on a cliff overlooking Ingonish Harbor.
"For live music during the Celtic Colours Festival, the Art Centre, in Inverness [16080 Hwy. 19; 902/258-2533; invernessarts.ca], is your best bet," says Michael Rankin, the Rankin sisters' nephew, who tends bar at the Red Shoe Pub.—Doug Cooper
A Wine Lover's Retreat on Long Island's North Fork
Though the upper eastern tip of Long Island—a 30-mile strip with oceanside plains, tidy villages, and rows of grapevines—has already been discovered, it's still a quiet alternative to the nearby Hamptons. Plus, its emerging wineries produce top-notch wines that are showing up on menus across the country.
What to Do
Start in the town of Southold at The Old Field (59600 Main Rd.; 631/765-0004; theoldfield.com). Owners Chris and Ros Baiz will give you a history of the Fork's viticulture as they pour you a glass of their red Rooster Tail. Nearby, Michael and Paula Croteaux run Croteaux Farm Vineyard (1450 South Harbor Rd., Southold; 631/765-6033), the only winery in the United States dedicated solely to rosé.
Where to Eat
In Greenport, the Frisky Oyster (27 Front St.; 631/477-4265; thefriskyoyster.com; dinner for two $90) is true to its name—the lively bivalves here range from the local island variety to ones from as far away as Oregon. Right on the harbor, Scrimshaw (102 Main St.; 631/477-8882; scrimshawrestaurant.com; dinner for two $120) serves fresh sea-scallop ceviche. At the North Fork Table & Inn (57335 Main Rd., Southold; 631/765-0177; dinner for two $120), the cod cake with black-truffled tartar sauce is as addictive as the warm cinnamon-cream doughnut holes.
Where to Stay
Check into the recently opened Shinn Estate Farmhouse (2000 Oregon Rd., Mattituck; 631/804-0367; shinnfarmhouse.com; doubles from $225). The four rooms look out on the property's vineyard, and the floors are lined with pine, fir, and oak.
"The Normandy fondue at the Village Cheese Shop [105 Love Lane, Mattituck; 631/298-8556; fondue for two $25]—made with Époisses and Saint Albray—goes great with a glass of our crisp Merlot 314 rosé," vintner Michael Croteaux says.—Charlotte Druckman
Hiking in New York's Catskill Mountains
Just over an hour's drive from New York City, the Catskills have become the urbanite's backyard: full of stylish restaurants, boutiques, and art galleries. The relatively unknown mountain hamlet of Phoenicia is the perfect base for fall hiking.
What to Do
Gear up for your hike with a guidebook and map at the Nest Egg bookshop (84 Main St.; 845/688-5851), then hit the trail: three-mile Giant Ledge (Ulster County Rd. 47, 10 miles west of town), which has panoramic views of 4,180-foot Slide Mountain. Or, trek up the nearby Belleayre Mountain—a ski run in the winter—to see the entire yellow and bronze valley below.
Where to Eat
Plate-size blueberry pancakes are what they're known for at Sweet Sue's (49 Main St.; 845/688-7852; breakfast for two $25), run by Sue Taylor. Assemble a picnic for your hike at the Phoenicia Delicatessen (46 Main St.; 845/688-5125), where the grandmotherly Margarete Nolte makes a stellar German potato salad. Brooklyn-born chef Devin Mills, who trained at New York's Le Bernardin and Gramercy Tavern, opened Peekamoose (8373 Rte. 28; 845/254-6500; peekamooserestaurant.com; dinner for two $65) in the neighboring village of Big Indian in 2005. The red wine-braised beef short ribs are the biggest crowd-pleaser.