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CONNECTICUT
Litchfield Hills
Meandering along the curvy wooded roads in and around Litchfield. you’ll find numerous antique shops and roadside cafés, even if you’re not shopping for the next great piece of art for over the sofa. The town of Woodbury has dozens of antique shops, and is closely followed by other towns in the northwest Connecticut region.

Culturally, Litchfield has an array of options, from a small but inspiring gallery scene and the annual Litchfield Jazz Festival (this year August 6–8, www.litchfieldjazzfest.com) to the world-renowned, earth music innovator, the Paul Winter Consort (www.livingmusic.com). Winter and company have for the past 14 years been performing solstice celebrations at New York’s St. Patrick’s Cathedral, and tour the world the rest of the year with their “Living Music” concerts. Look locally for small gigs at intimate venues. A stroll around the bucolic grounds and galleries of Wisdom House (www.wisdomhouse.org), an interfaith sanctuary with Peace Gardens and outdoor labyrinth, is a wonderfully relaxing afternoon walk.

You do yourself a great disservice not to take a romantic stroll or hike in this area’s great outdoors. There’s a nice, walkable chunk of the Appalachian Trail here, and Litchfield’s 4,000-acre White Memorial Conservation Center (www.whitememorialcc.org) has 35 gorgeous miles of trails for hiking or unparalleled cross country skiing in winter, as well as interpretive trails in wetland marshes, a boating lake, and a quaint nature museum. Plenty of ponds, lakes, rivers, and reservoirs fill hilly vistas through your windshield as you set out exploring. One of our favorite things to do is get intentionally lost on back roads, then when we get hungry or just feel our country drive has come to an end, flip on that navigator of the new century, the GPS, and get ourselves back to civilization. Being real estate junkies, we find lots of homes to covet this way as well. Bringing home some of the amazing native flowers is easy (even simpler online) from Litchfield’s famous White Flower Farm (www.whiteflowerfarm.com), one of the nation’s foremost nurseries and horticultural centers (also a great afternoon’s walk).

More commerce-driven afternoons can be spent in Litchfield’s quaint downtown shopping streets, as well as in neighboring villages in the county. Clothing, art, crafts, and garden supply shops nestle between brick-fronted cafés and pubs. Local products and fine-flavored simple food are the hallmarks of Carole Peck’s Good News Cafe (694 Main Street So, Woodbury. Tel: 203-266-4663. www.good-news-cafe.com)—try the organic roast chicken with buttermilk mashed potatoes. It can be tough to get a table at contemporary West Street Grill (43 West St, Litchfield. Tel: 860-567-3880. www.weststreetgrill.net), but if you can snag an outdoor spot, do, for people watching and enjoying sun-dappled village greens overseen by white-steepled churches. In spring and autumn, the flora of the entire county is every amateur photographer’s dream.

THE HIDEAWAY: WINVIAN
The history-making gay wedding featured in Martha Stewart Weddings last June happened at the dreamy Connecticut compound of eclecticism called Winvian. We would hold our nuptials here in a heartbeat. This is the most over-the-top property you might imagine while still maintaining a cheeky elegance and never veering into amusement park territory. On 113 acres of pastoral meadow and woodlands, there are 18 cottages, each created by a different architect and designer. The building styles are wonderously diverse, from stone lodge or red barn to Masonic temple and tree house—there’s even an entire helicopter fuselage inside one cottage, and a stick beaver lodge over the bed in another. From the interior of our deluxe cabin, “Woodlands,” we could be forgiven for forgetting we’re not outside. Full-size trees soar over the enormous, double high room, the sinks are made from tree trunks, there is a stone waterfall that separates the bed from the sunken tub that overlooks the forest through a floor-to-ceiling picture window. Glass everywhere lets in copious light, and the two-sided stone fireplace emits a glow into both living room and bedroom. Lock the door, I’m never leaving. The bar, stocked with the spirits we requested before arrival, is not quite sustenance enough, so we walk the winding paths to the restaurant. Several rooms in the historic main house have a few tables each, and the food is elegant and international, with three-course menus (included in the rate, as is all food and drink, picnics, cocktail hour, and afternoon tea). My handmade pasta with diver scallops was superb, and the lamb duo (loin chop and shank tartellette) was out of this world. 155 Alain White Rd, Morris, CT. Tel: 860-567-9600. All-inclusive stays start at $1,250. www.winvian.com

MAINE
Kennebunkport
After a long weekend in Kennebunkport, I would have thought I’d grown barnacles behind my ears. Super-nautical Kennebunkport (pronounced Kinny-Bunk by Mainers) has more than its share of silly souvenir shops with lobsters and lighthouses, but the people couldn’t be more welcoming, the food is outrageous, and romance abounds. There is also lots of upscale, boutiquing and antiquing to be done in the very walkable downtown. A longer stroll along the rugged coast bordering Ocean Avenue brings us past some of the most elaborate seaside mansions imaginable, and they all pale in comparison to the summer residence of George HW Bush and family—truly one of the most magnificent residential properties in the country. By the time we make it all the way out to the Bush compound and back, our feet are aching and stomachs rumbling.

CLICK FOR SLIDESHOW OF NEW ENGLAND

THE HIDEAWAY: HIDDEN POND
There’s something about the fairytale fantasy of a Maine cottage in the woods to which people really respond. Birdsong and butterflies in the meadow, a babbling brook, perhaps a few deer (or moose) prancing through the underbrush and wildflowers…at first glance, this elegant enclave of cottages just up the road from Goose Rocks Beach seems like the fairytale come true. You ain’t seen nothing yet. Among 60 acres of balsam and birch, 14 one- and two-bedroom cottages are a fiesta of style and quirkiness once you open the door. Each interior has been designed by a different Maine-based artist, and their styles are eclectic to say the least. Our cottage, called “Day Dream,” is a mix of birch branches around mirrors and bed headboards and rustic, natural touches with a counterpoint of an ultra-modern galvanized steel wall and a green neon tube running vertically up another wall. Other cottages have contemporary or classic themes, from East Indian to Euro-chic, but the common denominators are stone fireplaces, sexy outdoor showers, Frette linens, nicely sized private kitchens (in which you can have cooking classes or have a private chef if you don’t want to do your own thing), and gargantuan screened porches with overgrown daybeds, rockers, tables, and soft blankets for napping. The resort also has a small gym (the cardio cottage), swimming pool, bicycles, and pick-your-own organic garden if you’d like to bring a bouquet back to your digs. Every morning is like Christmas as we wait for my favorite service detail among so many brilliant service examples. Delivered to our door, hanging from a special hook, is a thermos of hot coffee, fresh-squeezed juice, and just-baked breads and pastries each morning with the newspaper rolled up alongside. I knew I was going to like the couple that owns Hidden Pond the moment I met them. When we walked into the Back Porch Lounge and both Tim and Juan were drinking Maker’s Mark Manhattans (my drink). We spent a terrific evening chatting about the property, the surrounding area, and their wedding at the resort two weeks before opening last year. 354 Goose Rocks Rd, Kennebunkport, ME. Tel: 207-967-9050. Cottages start at $425. www.hiddenpondmaine.com

MASSACHUSETTS
Boston
I had never spent time in Boston, so the opportunity to enjoy a long weekend strolling the tree-lined brick streets of the picturesque South End seemed like a big win. “The gay community in town has become so integrated over the past few years,” a Bostonian friend told me. “Go into any gay bar and it’ll have a good percentage of women and always some straight people too.” That happy harmony seems to pervade the entire South End with its very specific architecture (the nation’s largest collection of Victorian, brick, bow-front homes of five to six stories with ornate wrought-iron railings on the stoops). The Tremont Street corridor is filled with unique boutique shops, resto/bars (local laws require food to be served to procure a liquor license, so there are no solely spirit-serving bars), and bistros bustling with al fresco diners during nice weather. Vintage clothing, wine, cheeses, housewares, décor, and a lovely large smattering of rainbow flags draw an artsy crowd of visitors, matching the creative types who are resident here. It’s got a very bohemian feel that is incredibly welcoming.

Lunch at Stephi’s on Tremont (571 Tremont St, Boston, MA. Tel: 617-236-2063. www.stephisontremont.com) is asserted as the best bet along these lanes. The signature salads and comfort food, like cheddar-stuffed meatloaf or three-cheese mac, are what brings neighborhood diners back again and again. Sitting in the big leather booths, we see lots of giant burgers being relished, so I order the same. A sirloin classic, it is huge and juicy with slab bacon, sautéed mushrooms, and caramelized onions. Definitely a multi-napkin meal. There are same-sex couples and groups of laughing friends, plus a few business types all enjoying the dark table, wood-hued, clubby atmosphere. Dinner is a jaunt to the recently opened W Hotel with the new favorite table to secure in town at Market by Jean-Georges Vongerichten (W Boston, 100 Stuart St, Boston, MA. Tel: 617-310-6790. www.marketbyjgboston.com). Intended to highlight the best dishes this super-chef has created, the international menu features classics that JG fans will fondly recognize. The rice cracker-crusted tuna with citrus-chili emulsion is perfection, soy-glazed short ribs with apple-jalapeno puree and savory rosemary crumbs is stick-to-your-ribs wonderful, and the service (from what our gaydar tells us is a very gay staff) is spot-on. The assuredness and flair of this restaurant makes it, currently, the talk of Beantown. A nighttime stroll over to Boston Common and the Public Garden makes a perfect, post-prandial meander.

THE HIDEAWAY:
CLARENDON SQUARE INN
The best part of a B&B experience is feeling like you’re staying in the home of friends…but I’ve rarely found that the B&B-owning friends and I have much in common, and certainly not in decorating sense. There’s not a doily to be found in this hidden, hip, boutique inn. Owner Stephen and his partner, Bobby, are extra-gracious hosts with advice and suggestions, but none of the fawning found around so many B&B breakfast tables. This six-story brick townhouse has no sign out front (I later saw a tiny brass plaque by the lower door). Two rooms or one luxury suite per floor, an outdoor dining patio, and a hot tub deck on the roof make each well-styled tableau feel personal. The modern art, glass sculpture, and bookshelves filled with travel books and Eastern tomes feel worldly and expansive instead of claustrophobic, as other tiny inns can seem. The room on the top floor is masculine and contemporary with saturated earthtones and a white marble fireplace. The Clarendon Suite is apartment-sized and features architectural details (all lovingly restored/overseen by Stephen in a strip-to-the-studs rehab) like barrel vaulted mahogany ceilings, free-standing soaking tub, and eight-foot walk-in shower. This is definitely a spot where you would hang the “Do Not Disturb” sign on the knob…but nobody here will disturb you anyway. 198 West Brookline St, Boston MA. Tel: 617-536-2229. Rooms from $115. www.clarendonsquare.com