Plan Your Holiday Tour and Discover Your Future Community
The holidays are perfect for embracing festive cheer, exploring new towns, and envisioning your future home. These NYC suburbs don’t just deck the halls—they transform them into postcard-perfect celebrations of the season, offering the kind of charm and community spirit you’d love to wake up to year-round. So, grab your holiday list and plan your suburban tour because these towns are just as magical to visit as they are to live in.
WESTCHESTER
Armonk, NY: Frosty’s REAL Hometown
Armonk, NY might just be the origin of “Frosty the Snowman,” and the town celebrates it like it’s true. Picture Main Street filled with entertainers, train rides, and a holiday parade capped by a sparkling tree lighting. Start your day at Beascakes Bakery for mini donuts that are just as sweet as the town itself. Whether you’re visiting or imagining your life here, Armonk’s small-town vibe and big holiday energy make it a place that feels like home.
Chappaqua, NY: Small-Town Magic All Season Long
Chappaqua offers the kind of downtown charm that makes you want to linger. After breakfast at Bobo’s Cafe, head to the Great Holiday Train Show at the historic Horace Greeley House, where vintage trains wind through a festive wonderland. Later, stroll to Scattered Books, an independent bookstore with a cozy, community feel. End your day at Le Jardin du Roi, where French onion soup and mussels feel like a warm hug on a cold winter night. Visiting Chappaqua during the holidays gives you a glimpse into its close-knit community—and what it might feel like to call it your own.
Mount Kisco, NY: Caroling and Community Spirit
Mount Kisco’s annual tree lighting at Village Hall Green is everything a suburban holiday should be: warm, welcoming, and a little magical. This event celebrates the town’s communal spirit, from ukulele carolers to kids’ choirs. Plan to visit, donate to the local food pantry, and soak in the charm that makes Mount Kisco feel like home during the holidays—and every other day of the year.
Tarrytown, NY: Festive Markets on the Hudson
Tarrytown’s TaSH Holiday Market isn’t just about shopping—it’s about experiencing a town that feels alive with holiday spirit. Grab a bite at the cozy Tarry Tavern and hop on the Holiday Trolley, which connects you to Sleepy Hollow’s festivities. Picture local shops, riverside charm, and tree lighting that makes you wish the season lasted forever. Whether you’re visiting for the day or imagining a future here, Tarrytown invites you to settle in.
CONNECTICUT
Greenwich, CT: A Festive Wonderland
Greenwich glows during the holidays, literally. Twinkling lights line the streets while the Greenwich Reindeer Festival brings live reindeer and Santa himself to town. Boutique shopping along Greenwich Avenue offers everything from high-end finds to unique holiday gifts. Visiting Greenwich feels like stepping into a holiday postcard, but it also gives you a glimpse of a town that balances vibrant community events with everyday luxury living.
Stamford, CT: Dazzling Displays and Holiday Magic
Stamford takes the holidays to the next level. The immersive Holiday Wish Express at Stamford Town Center sparks a sense of awe in kids and adults alike. A visit to Stamford reminds you why many people love calling this dynamic city home—especially during the holidays.
Norwalk, CT: Global Traditions and Underwater Magic
Norwalk knows how to celebrate. Kids and adults can explore global holiday traditions at the Stepping Stones Museum. At the same time, at the Maritime Aquarium, Santa dives with sharks in a one-of-a-kind underwater holiday show. Add in a screening of Rudolph the Red-Nosed Reindeer 4D Experience, and you’ve got a holiday visit that’s equal parts fun and memorable. Norwalk delivers if you’re dreaming of a town with creative energy and community spirit.
Fairfield, CT: Trains and Timeless Holiday Fun
Fairfield’s Holiday Express Train Show is a must-see for train enthusiasts (or anyone who loves a nostalgic holiday moment). Model trains wind through snowy villages, sparking joy and wonder. The family-friendly atmosphere and charming downtown scene make Fairfield feel like a festive town during the holidays and a great place to settle down.
NEW JERSEY
Princeton, NJ: Timeless Elegance and Holiday Spirit
Princeton’s Palmer Square Christmas Tree is iconic, but this town offers more than just holiday eye candy. Stroll through the Morven Museum’s Festival of Trees, take a historical walking tour, or warm up with mulled wine during the Holiday Wine Trails Weekend. It’s a town that balances intellectual charm with cozy holiday traditions—a perfect mix for those seeking a community with depth and vibrancy.
Cranford, NJ: A Trolley Ride to Holiday Joy
Downtown Cranford sparkles during the holidays with its creative Christmas trees, festive trolley rides, and a nostalgic lineup of holiday movie screenings at the local theater. This town is where the holidays feel deeply personal—shopkeepers know your name, and Santa’s mailbox waits for every child’s wish list. Imagine living in a town where every day has a bit of that warm, connected feeling.
Summit, NJ: Festive Fun for All Ages
In Summit, the holidays turn into a game of hide-and-seek, with over 100 elves hidden throughout downtown shops and restaurants. From horse-drawn carriage rides to ice sculpture demos, Summit invites you to explore its streets and taste its warm, vibrant community. It’s the town that makes you want to stay a little longer—and maybe even call it home.
LONG ISLAND
Jericho, NY: Christmas Every Day
At Milleridge Inn Village, every day is Christmas. This historic spot in Jericho is a year-round holiday destination with its charming Christmas shop, bakery, and specialty stores. During the holidays, the magic is turned up a notch, offering visitors a timeless experience—and a glimpse into the kind of town where holiday cheer lasts all year.
Port Washington, NY: Coastal Charm Meets Holiday Magic
Port Washington’s waterfront becomes a sparkling backdrop for the holidays, with its quaint streets lined with lights and community celebrations that feel straight out of a Hallmark movie. Whether you’re window-shopping, dining, or taking in the seasonal glow, this town exudes warmth and charm. It’s easy to see why so many people fall in love with Port Washington during the holidays—and stay for a lifetime.
Oyster Bay, NY: History and Holiday Spirit
Oyster Bay offers a unique mix of historic charm and festive celebration. Visit Planting Fields Arboretum, where the holiday decorations are as lush as the surrounding greenery, or stop by Sagamore Hill, Theodore Roosevelt’s former home, for a taste of history wrapped in seasonal cheer. This small coastal town captures the magic of the holidays and the essence of a tight-knit community.
Plan Your Tour (Picture Your New Hometown)
These holiday towns aren’t just magical to visit—they’re amazing communities to call home. As you tour these festive destinations, let the twinkling lights, bustling markets, and warm community vibes guide you. Whether envisioning a move or just looking for holiday cheer, these NYC suburbs deliver all the charm and connection you could want—during the holidays and beyond.
For more insights, visit SJ’s New York City suburbs section and the New York City blog page on our website.
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