America’s Liveliest Holiday Traditions from Coast to Coast

30 ways to celebrate the season like a local.

Compass
Compass Quarterly
7 min readNov 4, 2016

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Illustrations: Saskia Rasink

Surround yourself with Basalt’s seasonal sounds

“There’s nothing like an evening of music following a day on the Aspen slopes — and the downtown district of Old Town Basalt presents options of every kind. A DJ spins nightly at burger-and-beer destination The Brick Pony Pub (1), temporarily replacing its saloon ambiance with a dance floor. Soak in live Spanish guitar melodies over tapas at Tempranillo (2). Or duck into Heather’s (3) for its acoustic folk set and hearty, housemade savory pies.”
— Basalt Broker Associate Richard Duddy

Venture to Colorado’s most rugged real estate

Cookhouse:
“Located 12 miles from Aspen, just beyond the former mining town of Ashcroft, is the Pine Creek Cookhouse (4). Its ski-to-lunch consists of a mile-and-a-half climb that culminates with hearty fare, crackling embers, and a cozy bar. Over-imbibe? Take the horse-drawn sleigh back down.”

Cabin:
“For a kid-friendly splurge, reserve a table at Snowmass Mountain’s Lynn Britt Cabin (5). After ascending 9,200 feet by snowcat, enjoy a locally-sourced feast (think elk stroganoff and whiskey-tinged bread pudding) in the elegantly rustic space, surrounded by majestic peaks.”

Hut:
“Escape the fray with an overnight at the 10th Mountain Division Huts (6), 34 backcountry retreats built to honor the WWII soldiers who trained nearby. Firewood is supplied; just bring rations, sleeping bags, and hiking gear.”
— Aspen Broker Associate Mary Anne Meyer

Experience San Francisco all aglow

Illuminate SF (7), the public art initiative, holds its annual Festival of Light from Thanksgiving to New Year’s Day. During this period, the luminous work of famed experiential artists such as Leo Villareal, Daniel Libeskind, and James Turrell comes to life at dusk, staying on until midnight every evening. Employing 25,000 eco-friendly, LED lights, more than 30 installations span 12 neighborhoods, with guided tours and artist panels in regular rotation. A concentration are found along Market Street from the Embarcadero to Van Ness Avenue, making the thoroughfare an ideal starting point to take in the twinkling sights.”
— San Francisco Founding Agent Neal Ward

Embrace holiday extravagance at SoCal’s most over-the-top events

The tallest trees…
“Lined with pines, San Marino’s Saint Albans Road is nicknamed Christmas Tree Lane (8). For 50 years residents here have lit the 150-foot giants, wowing kids and adults alike.”

The biggest slumber party…
“Nab a prime spot for the Rose Parade (9) by camping on Orange Grove the afternoon before. It’s a night of caroling, sidewalk grilling, and card games, a Pasadena tradition!”

The fanciest tailgate…
“At the foot of the San Gabriel Mountains, Pasadena’s Langham Huntington (10) hotel is a homecoming hub for families and Rose Bowl fans, who catch up over Wagyu sliders and lobster corn dogs in its stately Tap Room.”
— Pasadena Estate Director Brent Chang

Be transported by Santa Barbara’s outdoor offerings

Cycle:
“Locals and the pros who train here swear by The Goob Loop (11), which winds around Gobernador Canyon Road. Plus, December’s low tides are perfect for pedaling miles on the hard-packed sand. At Santa Barbara Bikes To-Go, rent premium bikes for the trek — deliverable right to your hotel door.”

Sail:
“A cherished tradition is the Santa Barbara Parade of Lights (12), a coastline processional of light-adorned boats that culminates in fireworks. Look on from Leadbetter Beach or Stearns Wharf pier, or, better yet, reserve a ride aboard the Double Dolphin yacht and experience it up close and personal.”

Rev:
“Mount your motorcycle and rumble over the spectacular Santa Ynez Mountains to the 19th-century stagecoach stop Cold Spring Tavern (13). Tucked beneath a canopy of trees, soak up the live blues, snag a steak cooked to order on the open grill, and kick back a glass from their vast list of Central Coast reds.”
— Santa Barbara & Montecito Senior Estate Director Pamela Regan

Fill your calendar with Manhattan’s finest cultural events

As a longtime patron of the city’s many esteemed institutions, NYC Head of Luxury Sales Kyle W. Blackmon takes every opportunity to enjoy the season’s plentiful pursuits and artistic offerings.

November 30:
Kick off the season with Alvin Ailey American Dance Theater’s Opening Night Gala (14), which inaugurates the dance company’s winter series with an infectious blend of jazz, ballet, modern dance, and live gospel.

December 16–18:
Join the New York Pops (15) for their two-night run at Carnegie Hall, where the program includes a mix of classic and contemporary holiday tracks.

December 20:
Put your own pipes to the test at Lincoln Center. Their yearly Messiah ‘sing-in’ (16) invites the 3,000-plus attendees to serve as the chorus in Handel’s inspiring score.

Elevate winter evenings at New York’s high-altitude bars
During the frosty months, the city’s aerial bars transform. The Roof (17), occupying the 29th floor of the Viceroy Central Park hotel, boasts glistening panoramas of the iconic green space from its lamp-lit West 57th Street vantage, while the Refinery Hotel (18) proffers Empire State Building views and a couch-flanked fireplace. Further downtown, La Birreria (19) in Eataly’s penthouse is reinvented as a life-sized snowglobe.
— NYC Real Estate Broker Kimberly Lyn Pressman

Take time to celebrate the Mid-Atlantic’s autumn bounty
Tree-lined monuments, landscaped plazas, food festivals aplenty — the nation’s capital excels at fall. Washington DC Realtor Gina Russo shares the best ways to take advantage within the Beltway and beyond.

If you have 45 minutes…
Stop by Mount Pleasant Farmers’ Market (20). “This Lamont Street gem is my go-to grocer. In addition to just-picked veggies, score seasonal flowers and from-scratch pies.”

If you have an afternoon…
Drive to Homestead Farm (21) in Poolesville, Maryland. “Gather honeycrisps in the orchard or venture into the fields to select pumpkins at this working farm. The picturesque foliage along the George Washington Parkway is a nice bonus!”

If you have a weekend…
Book a stay in Middleburg, Virginia (22). “Make a wine country reservation at the luxurious Salamander Resort & Spa or the historic Red Fox Inn & Tavern, then relax in the vineyards, brimming with grapes from Cabernet Sauvignon to bubbly.”

Enjoy the unexpected appeal of the Hamptons’ off-season
While summer is undoubtedly the East End’s most popular time of year for visitors, the region’s permanent residents are privy to a host of perks. Here, three examples that make a case for a wintertime jaunt on Route 27, as suggested by Hamptons Real Estate Salesperson Bill Williams.

Trade Waves for Currents
You can’t beat the area’s peaceful waterways during fall’s striped bass season (23). Going out with an expert guide like David Blinken of North Flats will ensure an amazing day on the water, learning about the art of fly fishing as well as breathing in the Peconic Bay surroundings.

Bare Branches, Better Views
Take advantage of the opportunity to view some of the country’s most fabulous real estate — usually sequestered behind manicured rows of shrubbery — in East Hampton’s estate section (24). Start your tour on Lily Pond and Further Lanes.

Wine Without the Wait
The tastings at Wölffer Estate Vineyards in Sagaponack (25)and Channing Daughter’s Winery in Bridgehampton (26) are very popular with tourists, but during a fall visit one can enjoy a more mellow experience amid the Riesling and Cabernet Franc vines.

Create new holiday traditions in Miami
In the international hub of Miami, festivities reflect customs from around the globe, and the holidays are no exception. “In most Central and Latin American countries, Christmas Eve, or Nochebuena, is the key celebration, with families gathering to drink and dine,” says Miami agent Yasser Ponce. To get a taste, head to the Magic City boulevard of Calle Ocho and beyond for Christmas, Cuban-style.

First stop — Toast the holidays at home
Crema de Vié (27) is a sweeter, more high-spirited cousin to egg nog. “Whip up sugar, condensed milk, egg yolks, and vanilla, then spike liberally with rum!”

Second stop — Dine at Versailles Restaurant
Since 1971, this famous café has served authentic Cuban fare in southwest Miami, especially “rich, roasted pork (28)and fragrant congri (29), a mix of rice and black beans.”

Third stop — Indulge at Pinocho Bakery (30)
Buñuelos, my favorite dessert, are yucca fritters with a hint of anise in a light syrup. They’re best homemade, but this Coral Gables legend has them down pat.”

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Compass
Compass Quarterly

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