Best Women's Clothing, Berkshires
Gatsbys
Don't be fooled by the faded shabby-chic exterior: Beyond the white wicker sidewalk furniture is a shop stylish enough for any city's streets. Buyer Pamela Fink stocks Gatsbys with premium products including Paper, Denim & Cloth and True Religion denim; Theory tops and trousers; and a rainbow of Petit Bateau T-shirts. There's also a selection of sporty shoes, Cosabella lingerie, Kiehl's products, and Juicy Couture loungewear. 25 Railroad St., Great Barrington, MA
Best Men's Clothing, West
Mr. Sid
Head west, young man, to Newton Centre. There you'll find Mr. Sid, the shop that caters to classy guys looking to dress to the nines in Armani, Hugo Boss, Zegna, and Corneliani. Helpful, knowledgeable, and courteous salesmen escort customers through the store, which is divided into smaller areas by collections. Tired of shopping? There's an in-store pool table, a hair salon, and a well-stocked bar. 1211 Centre St., Newton Centre, MA http://mrsid.com/
Best Bowling Alley
Sacco's Bowl Haven
Photograph by Bob O'Connor There are flashier lanes in town—theme park-like emporiums with flat-screen TVs and signature cocktails. But the laid-back atmosphere of Sacco's wins it top honors. It's complete throwback awesomeness, from the candlepin setup to the pencil-and-paper mode of scorekeeping. If there's a wait, grab a seat at the bar, order a Flatbread Company pizza and a Pretty Things pint, and kick back. 45 Day St., Somerville, MA 2144,
Best Jewelry
Dorfman Jewelers
Yes, there's loads of ice on hand here, in the form of Patek Philippe timepieces and Henry Dunay necklaces, but the warm and patient service at Dorfman will thaw any notion that buying big-time bling is a daunting endeavor. In business for seven decades and counting, the family-owned jeweler caters to both Beacon Hill bluebloods and a younger, funkier clientele with diamonds and pearls aplenty, vintage-inspired house lines, and New England's only Van Cleef & Arpels salon. 24 Newbury St., Boston, MA 2116,
Best Stationery
Bob Slate Stationer
Old souls who still prefer old-fashioned card stock to Evites may get carried away when shuffling through the pens, pencils, and paper of every possible type at Bob Slate. For an extra-personal touch, you can work with the store's knowledgeable and creative staff to custom design your own full set of embossed, 100-percent cotton stationery, a move that will have you leaving your calling card all around the city. 1288 Massachusetts Ave., Cambridge, MA 2138, http://bobslate.com
Best Women's Clothing, Vintage
The Haberdash Vintage
When Amy Chase's online selection of '60s-era boots, sequin tops, fur-trimmed coats, and accessories grew too big for Etsy, Chase found herself trolling for vintage trailers. Now she stations her Bellwood camper at outdoor markets, festivals, and parking lots, and books private shopping parties with her movable boutique, the Haberdash Vintage. 138 Green St., Worcester, MA 1604, http://haberdashvintage.com
Best Jewelry, Designer Collection
Royal Jewelers
Chances are the jewelry you saw on the pages of a national fashion magazine is under the glass at Royals. Penny Preville, Kisselstein-Cord, SeidenGang, Doris Panos, TechnoMarine, and Philippe Chariol are just some of the designers represented at this family-run business, which has catered to the North Shore area for 50 years. Look for a store face-lift this fall that will add an in-house David Yurman boutique. 58 Main Street, Andover, MA http://royaljewelers.com/
Best Women's Shoes
December Thieves
When Lana Barakat decided to rethink her two Beacon Hill clothing-and-gift boutiques, she envisioned one store catering to home décor and another specializing in apparel and accessories. This divide-and-conquer strategy created more room for something Boston has been sorely lacking: high-end women’s footwear. Handcrafted by European and American designers, Barakat’s collection includes everything from metallic leather boots with an offset heel to cheetah-print loafers to sneakers with a velvet knot tie—perfect for navigating the cobblestones in style as you stroll up Charles to check out what other treasures await at the December Thieves home store. 51 Charles St., Boston, MA http://decemberthieves.com
Best Clothing, One-Stop Shopping
Louis Boston
Buyer Debi Greenberg scours the globe to find the in fashion for men and women alike. Her Back Bay store is known the world over for its incredible timing, with many design darlings of the fashion press finding their way onto its floors before they hit the big time. The store caters to a wide variety of ages, from street fashion on the ground floor to power suits on the second and third levels, and a mix of women's wear designers from Kiton to Imitation of Christ. There's also an extensive and cutting-edge makeup counter, Salon Mario Russo, and a top-notch restaurant. 234 Berkeley St., Boston, MA http://louisboston.com/
Best House Cleaner
The Maids Home Services
We aren't ones to cry over spilt milk, as our floors can attest; our couch has more hair on it than our cat. Without a speck of judgment, the Maids clean up our act month after month, dusting baseboards, degriming showers, and all but eliminating any traces of pet (except for, of course, the pet itself). They're quick, well priced, and unobtrusive: Aside from the preternatural sparkle and neatly triangled toilet paper, you'd never know they'd been there. 179 Boylston St., Jamaica Plain, MA 2130,
Best Inn, Cape Cod
Roux
This saucy bed-and-breakfast brings a splash of urban charm to the outermost Cape. Rooms are painted bright colors—no staid New England décor here. The food stands out, too: At breakfast, dig into treats like caramelized-onion-and-shiitake clafoutis; by night, mingle with eclectic guests over gratis wine and snacks. 210 Bradford St., Provincetown, MA 02633, http://rouxprovincetown.com
Best Takeout, North
Grange Gourmet
On the quieter (i.e., not downtown Gloucester) side of Cape Ann, this erstwhile grange building is home to gourmet sandwiches, salads, a tiny seating area (great for local gossip) and a miniscule garden that will make you forget about the beach entirely. 457 Washington St., Gloucester, MA
Best Hotel, South
Mirbeau Inn & Spa
Sipping wine on a blanket by the cranberry bogs is so much more relaxing than sitting in traffic on the Bourne Bridge, isn’t it? With three restaurants, easy access to two golf courses, and a spa, the South Shore’s version of a turreted French manor is a welcome respite before the Cape Cod fray. https://plymouth.mirbeau.com
Best Neighborhood Diversion, North End
BCYF Mirabella Pool
Each summer, city dwellers of all stripes—sunbathing nonnas, bronzed Adonises, giddy teens—flock to this urban oasis, making it one of the top people-watching spots in town. Not to mention one of the best bargains: A season pass costs a mere $20. In other words, a whole lot less than a trip to the Cape. 475 Commercial St., Boston, MA 02109, http://boston.gov/community-centers
Best Wedding Coordinator
Hoople Popple
Hopple Popple founder Linda Matzkin and her daughter Abby Matzkin Gordon have the experience, eye for design, and romantic natures—not to mention respect for spending limits—to fashion truly dreamy weddings, be they barefoot-on-the-Cape or candlelight-at-the-Ritz affairs. 284 California St., Newton, MA 2158, http://hopplepopple.com