Midnight Marathon Bike Ride
Any long group bike ride is going to offer plenty of opportunities for bonding with your fellow cyclists, but the thrill of a moonlit journey through car-free streets on a path you know will be filled with determined marathoners in just a few short hours? That’s something special. There are glow sticks and dance music. Challenging inclines and exhilarating downhills. And a buzz like you’ve never felt before as you cross the finish line in the wee hours of the morning. crw.org.
Broadway Bicycle School
Not a shop for pricey equipment and attitude, but it does happen to be the place most couriers recommend. Have the expert staff fix your wheels, or fix them yourself: The school rents out shop space and tools for $6 an hour, rents all of the above and a private mechanic-instructor for $12 an hour. Roll in or make an appointment. If that's not cool, what is? 351 Broadway, Cambridge, MA .
Citizen Public House & Oyster Bar
The cocktails at this funky-meets-casual spot hit it out of the park—order the mezcal-based "No More Parties in Fenway" to channel your inner ’Ye before weaving through Sox traffic on your way home. 1310 Boylston St., Boston, MA 02215, citizenpub.com.
Winsor Dim Sum House & Bar
The beauty of this dim sum spot's new Quincy location is in the extensive, sharply executed menu: In addition to traditional cart service, diners can order dishes via checklist, which means the char siu-stuffed bao are fluffier, the wok-fried radish cakes are crisper, and the pea pod stems—prone to wilting and sogginess at lesser restaurants—still retain their vibrant color and delicate crunch. Bonus points for a full bar. 706 Hancock St., Quincy, MA 02170, winsordimsum.com.
The Bristol Lounge, Four Seasons Hotel
The foie gras of hamburgers is thick, juicy, and perfectly seared. Served on fine china and squeezed between a poppyseed bun with just the right amount of lettuce, onion, and tomato, this ground beef patty is actually worth its steep price of $15.50. Kick back in an armchair in the clubby room and enjoy a sloppy but oh-so-civilized lunch. 200 Boylston Street, Boston, MA fourseasons.com/boston/dining/the_bristol_lounge.
Thursdays on the Lawn, Loring-Greenough House
Everyone from the neighborhood gathers to feast at this weekly outdoor picnic featuring a farmers' market, food trucks such as Clover, roving musicians, and occasional outdoor movies after dark. All you need is a blanket. 12 South St., Boston, MA 02130, loring-greenough.org/thursdays-on-the-lawn.
Citizen Public House & Oyster Bar
The lauded whiskey list is reason enough for a visit, but the real draw is the “Pappy Meal,” a western-themed box with a 2-ounce pour of Pappy Van Winkle, the coveted Kentucky hooch. 1310 Boylston St., Boston, MA 02215, citizenpub.com.
Geraldine Cole, Style Your Threads
When your wardrobe starts to feel like the by-the-pound pile at the Garment District, it’s time to give Geraldine Cole a call. The fashion maven began her career working in the costume departments of various theaters, eventually starting Style Your Threads when friends kept asking her for outfit advice. She’ll organize and cull your closet (or "archives" as she calls it), put together the ultimate special-occasion ensemble, or even pick out the perfect gift. MA styleyourthreads.com.
Citizen Public House & Oyster Bar
Low lights, dark wood, and more than 200 whiskeys. As far as drinking goes, it doesn’t get much better than this. Prefer suds? No problem. The bar staff keeps a rotating line of draft beers and ciders that includes local stars such as Jack’s Abby and Downeast. 1310 Boylston St., Boston, MA 02215, citizenpub.com.
Aujourd'hui at the Four Seasons Hotel
It's nice of the attentive staff to give you space to conduct your business. Truth be told, as much networking gets done among the breakfast tables at this Four Seasons restaurant as at them; most diners spend their mornings circumspectly stealing glances past the potted palms to see who else is in the room, which all but hums with power. If that isn't enough to distract you, there's always the superlative view of the Public Garden. And the food (though predictably priced in the expense-account stratosphere) is worth five stars. Along with your fresh-squeezed juice, try the banana-stuffed French toast with strawberry syrup, the warm New England fruit compote, or the Japanese breakfast of grilled salmon, boiled egg, shiitake mushrooms, rice, seaweed, and miso soup, all on a black lacquer tray. 200 Boylston St., Boston, MA .
Bristol Lounge, Four Seasons Hotel
The Bristol is a refreshing respite from the cigar-chompin' clubbier bars around town, yet it still manages—with its white-coated waitstaff, marble bar tops, and Vose Galleries art—to maintain a stately feel. Maybe that's why visiting celebrities (Bruce Springsteen, Michael Jordan, Billy Joel) flock to its sofas and armchairs. Or maybe it's the signature martinis (stiff and serious, even in the more frivolous forms such as the green apple) and warm nut mix that keeps them coming back for more. 200 Boylston St., Boston, MA fourseasons.com/boston/dining/the_bristol_lounge.
The Bristol Lounge at the Four Seasons Hotel
Finger sandwiches, Scottish cones, Viennese pastries, English tea breads, pots of preserves, genuine tea caddies, and service stops at 4:30 p.m. on the dot. Hotel GM Robin Brown's standards are strict—as befits a bloke from Grantham, Lincolnshire. 200 Boylston St., Boston, MA .
<em>The Housing Project</em>, at the Boston Shakespeare Company
Choreographer Yoshiko Chuma presented one of the best constructions of the year.
Citizen Public House & Oyster Bar
Oysters, biscuits, and buttermilk-ricotta pancakesbrunch at this neighborhood tavern covers the bases. 1310 Boylston St., Fenway/Kenmore, MA 2215, citizenpub.com.