Peirce Farm at Witch Hill
While the Victorian mansion on this 19th-century estate in Topsfield boasts a Gilded Age past, it’s the newly refurbished 1873 barn that delivers memorably rustic events. Swap vows outside amid the foliage — and maybe even snap a pic with the property’s resident animals — before hightailing it to the transformed space. Inside, high-set windows stream in sunlight across hardwood floors, while a shimmering chandelier suspended from the two-story ceiling emits a soft glow for evening revelry. How’s that for romantic? 116 Boston St., Topsfield, MA 1983, peircefarm.com.
Bar 25
Sarah Walsh From the fruity rum-and-matcha colada to the Dragon’s Blood with mezcal, blood orange, and hibiscus, each drink at this Prohibition-inspired bar is inventive and totally Instagram-worthy. For the perfect date night, enjoy your craft cocktails with a side of mezze on one of the bar’s three floors. Hanging with a larger group? Go all out with a 12-glass champagne tower. 38 State St., Newburyport, MA 01950, bar-25.com.
Harbor Lounge
The million-dollar view from the Harbor Lounge, in P-town. / Photo provided by the Harbor Lounge This P-town bar has become the de facto cocktail klatch for the pre-cabaret and post-disco crowds, practically guaranteeing you’ll run into familiar faces from the South End gay scene. But the waterfront lounge attracts more than strictly LGBTQ vacationers thanks to floor-to-ceiling windows with views of the waves, as well as a pier where revelers rest stiff cocktails on rails and shoot the always-delightful breeze while the tide rolls in. 359 Commercial St., Provincetown, MA 02657, theharborlounge.com.
Hotel Commonwealth
Courtesy of Hotel Commonwealth With floor-to-ceiling windows and a string-lit terrace showcasing Green Monster vistas, Hotel Commonwealth’s new event space hits it out of the park. Part of the hotel’s recent $50 million makeover, the just-built wing is now the perfect spot for both Sox fans and culinary-minded couples to celebrate their love: The catering menu features dishes inspired by on-site hot spots Eastern Standard and Island Creek Oyster Bar. 500 Commonwealth Ave., Boston, MA hotelcommonwealth.com.
Hangar B Eatery
A top-notch brunch spot—on a tarmac? It's long been a reality in Cape Cod, where chef Brian Erskine turns out fluffy lemon-ricotta pancakes and hearty red-flannel hash from a kitchen at the Chatham Municipal Airport. Summer weekends find the place jam-packed, but you can pass the wait time on the second-floor deck watching the biplanes coming and going. 240 George Ryder Rd., Chatham, MA 2633, hangarbcapecod.com.
Flair Brides Maids
Christine Walber Colon knows bridesmaids play no minor role in pulling off a wedding, so she outfits them accordingly. Her third-floor suite carries the bright hues, comfortable fabrics, and flattering cuts of designers such as Charsa, Lynn Lugo, and Jenny Yoo. There are no wear-it-once sateen selections here—just gracious service and moderate prices. Finally, someone who gives the supporting cast its due. 10 Newbury St., Boston, MA 2116, flairbridesmaid.com.
Marathon Sports
Get personalized attention every step of the way at Marathon, where sharp-eyed employees will diagnose your stride on the sales floor and then bring out model after model in search of the right fit. (Customers are encouraged to take a test jog outdoors, too.) Be it Mizuno, Saucony, or other elite running shoe, your purchase is guaranteed to be ready for action—from a 5K to a stroll at the dog park—right out of the box. 671 Boylston St., Brookline, MA 2445, marathonsports.com.
Men's Suit Sale, Filene's Basement
Every fall and spring, rack after rack of Ermenegildo Zegna, Calvin Klein, Joseph Abboud, and other highbrow treasures are wheeled out onto the Basement's packed Downtown Crossing floor. They're the overstock and still-beautiful seasonal leftovers from upscale behemoths such as Bloomingdale's, Saks Fifth Avenue, and Barneys New York. And at prices that dip down to 70 percent off, you can snag two suits—plus tailoring—for the cost of one of their full-priced cousins. 426 Washington St., Boston, MA filenesbasement.com.
The Field
In Ireland, a pub is just a simple bar, not a junkyard of faux-Irish flourishes like County Cork mile markers or an imported floor. Behind the quaint red exterior of this Central Square spot is an unpretentious watering hole filled with friendly folks from students to punk rockers. Music from the corners, a ratty pool table, and comfy benches make it a great nightcap or Saturday afternoon haven. As for the most authentic measure of any Irish pub: The Guinness is positively soulful. 20 Prospect St., Cambridge, MA thefieldpub.com.
Woodward at the Ames
When you're looking for someone to pick up what you're puttin' down, try the Ames hotel's saloon, where a glass-topped bar and stainless steel accents lend an upscale gloss to the robust singles scene. If you're not ready to chat up a Financial District suit, head for the dance floor—or plot your next move while nursing a motivationally named cocktail, such as the "Skip and Go Naked." 1 Court St., Boston, MA 2108, ameshotel.com.
Landry & Arcari
Rugs lay the groundwork for a great room, but we've all been guilty of flooring faux pas. (Come on: Someone snapped up those geometric print '80s carpets.) Landry & Arcari has hundreds of timeless rugs. Choose from antique, Tibetan, traditional, floral, and French patterns, or order a custom piece you'll never tire of. Unlike that orange shag in the rec room. 333 Stuart St., Boston, MA 2116, landryandarcari.com.
Gallagher-Christopher Antiques
Even minimalists find joy in this boutique that flouts the typical dusty, cluttered antique shop. Gallagher-Christopher's selection includes 19th-century English dressers, early-20th-century lighting, and art deco chairs, along with the store's own new Hermes-esque orange lacquer boxes that, if not yet technically antiques, certainly deserve heirloom status. 84 Chestnut St., Boston, MA 2108, .
Paul Brown
If you've ever tried to make your own curtains, you know it's one of life's top-10 thankless tasks. Instead of spending weary hours over the Singer, call Paul Brown, who's been making swags for the stars since 1968. Whether you want gothic floor-to-ceiling velvet or the lightest sheers, your wish will be granted. 21 Drydock Ave., Boston, MA .
Mr. Sid
Is there anything out there more wonderfully old-school than Mr. Sid? The parquet floors; the in-house bar, hair salon, and billiards table; the genteel service—it all feels reminiscent of another time. The clothing itself is as current as it gets, however, with sharp styles from the likes of Ermenegildo Zegna, Brioni, and Scott James, plus a collection of high-end footwear. Men who prefer to go bespoke will appreciate the "made-to-measure" program, which offers custom clothing from a selection of the store's designers. 1211 Centre St., Newton Centre, MA mrsid.com.
Club Hollywood Boston at Ekco Lounge
Butches and femmes hoist their bottles together here on Saturday nights, when this Chinatown karaoke lounge and dance club becomes the closest thing lesbians have to a downtown clubhouse. Two levels of dance floors offer ample space for the mostly young and urban crowd to get down to electro, house, and hip-hop. Once a month, grrls slip on suits and fedoras (and boys and butches, dresses) for "drag karaoke." 41 Essex St., Boston, MA .