Visit, explore, and see what everyday life could look like beyond the city.
The holidays are the ideal time to explore the suburbs — twinkling lights, bustling main streets, festive markets, and that unmistakable feeling of community you can’t always spot on a random Tuesday in March. These towns don’t just decorate; they transform into full-on holiday destinations. And as you stroll, shop, taste, and tour, you’re also getting a preview of what life might feel like if you made the move.
Bundle up, grab your list, and get ready to explore these magical holiday towns in the NYC suburbs.
WESTCHESTER
Armonk, NY — Frosty’s REAL Hometown
Armonk does the holidays right with full Frosty-the-Snowman energy: entertainers, train rides, a parade, and a glowing tree lighting. Grab mini donuts from Beascakes Bakery, browse Hickory & Tweed for outdoor gear, and walk Main Street to feel the warmth of this close-knit northern Westchester gem.
Chappaqua, NY — Small-Town Magic
Chappaqua shines this time of year. After breakfast at Bobo’s Café, wander to the Great Holiday Train Show at the Horace Greeley House. Pop into Scattered Books for holiday reads, then settle into a long, cozy dinner at Le Jardin du Roi. Add a detour to Gedney Park for seasonal scenery.
Mount Kisco, NY — Carolers + Community
The annual tree lighting at Village Hall Green brings out the whole town — ukulele groups, children’s choirs, and tons of families. Grab a great gift at local shops like the beehive designer collective or Jolie Jordan, and don’t miss a treat from Bella’s Bakeshop.
Bronxville, NY — Classic Holiday Village
Bronxville transforms into a Norman Rockwell painting in December. Its walkable downtown fills with wreaths, white lights, and shoppers ducking into Park Place Bagels or Slave to the Grind. The village tree lighting and local chamber music concerts complete the picture-perfect vibe.
Rye, NY — Coastal Cheer & Classic Holiday Magic
Rye shines throughout the holiday season, with Purchase Street decked out in twinkling lights, festive window displays, and shops offering seasonal treats and holiday gifting events all month long. As you wander downtown, stop into Patisserie Salzburg or The Snackery Bake Shop for hot chocolate or a holiday dessert. Families also head to area parks, where December programming includes holiday bonfires, visits from Santa, and more. For a scenic break, wander through Rye Town Park or stroll the boardwalk near Playland, where the off-season quiet and sparkling shoreline make for a perfect winter walk.
Then cap off the day with dinner at Rye Grill & Bar or Ocean Blue Prime. With its waterfront beauty and welcoming downtown, Rye brings a warm, classic charm to the season.
Tarrytown & Sleepy Hollow, NY — Hudson Holiday Magic
The TaSH Holiday Market is the anchor, but don’t skip the annual holiday stroll, Lyndhurst Mansion’s festive décor tours, or the lantern-lit Holiday Market at Philipsburg Manor. Dine at Tarry Tavern or treat yourself to mint hot chocolate from Muddy Water Coffee & Café, voted best new coffee shop by Westchester Magazine.
Pelham, NY — Perfect for a Festive Holiday Stroll
Pelham’s holiday village vibe is second-to-none: small shops, locally owned cafés, and the Pelham Chamber of Commerce holiday events, which brings families out for extended shopping hours, festive window displays, and treats from local businesses along Wolfs Lane and Fifth Avenue. Stop into Pelham Art Center’s annual Handmade Holiday Craft Market, where regional artists and makers sell gifts and décor, or warm up with a latte from Flour Power, a neighborhood favorite.
CONNECTICUT
Greenwich, CT — Luxe Cheer
Greenwich truly glitters this time of year. Between the Reindeer Festival, Santa’s Workshop at Sam Bridge Nursery, and the glowing window displays along Greenwich Avenue, there’s no better place to be. Stop into Black Forest Pastry Shop for holiday sweets and do a little boutique browsing.
The celebrations continue throughout town. The Greenwich Holiday Stroll brings carolers, horse-drawn carriage rides, live musical performances, and dozens of festive in-store events along Greenwich Avenue and the surrounding side streets. Families love stopping by the Bruce Museum, which hosts seasonal exhibits and hands-on programs, or exploring the decorated grounds of Greenwich Point Park, one of the best winter walks in Fairfield County. Wrap up the day with hot chocolate from CFCF Coffee, a cozy dinner in Old Greenwich, or a visit to McArdle’s Florist & Garden Center, where holiday greenery, wreaths, and lights add even more magic to the season.
Stamford, CT — High-Energy Festivities
The Holiday Wish Express at Stamford Town Center immerses families in dazzling lights, themed rooms, and interactive walk-through holiday scenes, one of the area’s most popular seasonal installations. Afterward, head to Mill River Park’s Cohen Skating Center, where the outdoor rink glows under string lights and stays open through winter. Make a night of it with a warm meal at The Cottage or Hudson Social, both just a short walk from the park, and finish with hot chocolate from Glory Days Diner or a dessert run to Fortina, where the holiday buzz feels just as festive as the decorations.
Norwalk, CT — Creative, Coastal Holiday Fun
From Santa diving with sharks at the Maritime Aquarium to the global holiday traditions exhibit at Stepping Stones Museum, Norwalk keeps things playful. Add a stop at The SoNo Collection, where rotating holiday art installations, pop-up performances, and the large-scale “Season of Sparkle” décor pack in even more cheer. Cap your visit with waterfront hot chocolate at Harbor Harvest.
Fairfield, CT — Heritage, Holiday Markets, + Cozy Downtown
The Holiday Express Train Show at the Fairfield Museum & History Center is a longtime family favorite, with model trains winding through intricate winter villages that draw crowds every year. Just a short walk away, the Fairfield Holiday Shop & Stroll brings extended store hours, festive treats, carolers, and bright window displays to downtown. Inside the Fairfield Museum, historic galleries are dressed for the season, offering a warm backdrop to explore local history before heading back out to the twinkle-lit sidewalks. And no Fairfield visit is complete without a stop at Colony Grill for their iconic hot-oil pizza, a perfect warm-up after an evening wandering downtown’s festive streets.
Westport, CT — Artsy + Festive
Westport brings serious creativity to the holidays: the Downtown Holiday Stroll fills Main Street and Church Lane with twinkling lights, festive window displays, local shopping, and live music, while Winter Lights at Wakeman Town Farm offers lantern-lit pathways, farm animals, crafts, and cozy seasonal activities for families.
Stroll through Westport’s Main Street to see stunning boutique windows — many shops partner with local artists to create installations that draw crowds all season. Warm up with a seasonal latte at The Granola Bar, or grab a holiday doughnut at Coffee An’ Donut Shop, then wander over to the Westport Library, where December often brings author talks, pop-up exhibits, and community events that add to the town’s festive buzz.
| Want to know why the holidays are one of the best times to explore the suburbs? Read more in our post, The Holidays are Here! |
NEW JERSEY
Princeton, NJ — Historic Holiday Elegance
Princeton feels tailor-made for holiday strolling. Palmer Square’s Christmas Tree towers over the brick plaza, glowing against the backdrop of boutiques and cafés. Throughout December, visitors can catch horse-drawn carriage rides, meet Santa on weekends, and browse the square’s bustling holiday market pop-ups. Just a few blocks away, the Morven Museum & Garden’s Festival of Trees transforms each gallery with themed trees decorated by community groups — a local favorite for families. After touring campus or walking past Nassau Hall dusted with lights, warm up with mulled wine or cider from Teresa Caffe, then browse the independent shops along Nassau Street for gifts that feel handpicked and special.
Cranford, NJ — A Small-Town Holiday Movie, IRL
Cranford’s downtown turns into a full-on holiday village each December. The Cranford Christmas Tree Lighting, complete with live performances and a visit from Santa, kicks off a season of festive events. If holiday goodies are your must-have, check out the annual Holiday Treats & Sweets Walk happening in downtown Cranford on Saturday, December 13. Tour 14 local shops and restaurants, and score a special treat at each stop.
Once your crew is sufficiently sugared, hop aboard the Cranford Holiday Trolley, which loops through downtown with carols and colorful displays. After shopping, families stop by Track 5 Coffee for hot chocolate before catching a classic holiday movie at the historic Cranford Theater.
Summit, NJ — Family Fun and Downtown Sparkle
Summit brings the holidays to life with over 100 hidden elves tucked throughout downtown shops during the annual Elf Scavenger Hunt, a local tradition that draws families all season. Weekends feature horse-drawn carriage rides, roaming carolers, live ice-sculpting demonstrations, and extended shopping hours. At The Summit Playhouse, check out family-favorite Cinderella then head to restaurants like The Committed Pig and Summit House that buzz with festive energy. Add in the beautifully lit Village Green, seasonal maker markets, and the ease of strolling from shop to shop, and Summit becomes one of the most welcoming holiday destinations in North Jersey.
Maplewood, NJ — Creative, Community-Filled Holiday Warmth
Maplewood’s artistic spirit shines during the holidays. The Maplewood Village Holiday Lights celebration illuminates the downtown, while the Handmade Holiday Market at The Woodland showcases local makers, artists, and designers. Storefronts decorate with imaginative displays, families line up for the annual tree lighting, and Maplewood Village hums with shoppers grabbing gifts from beloved local shops like Words Bookstore. Warm up with a gingerbread cookie from The Able Baker and stroll over to Memorial Park, where the dramatic tree-lined landscape feels beautifully wintery.
LONG ISLAND
Port Washington, NY — Coastal Holiday Magic on Manhasset Bay
Port Washington shines during the holidays, especially along its waterfront. Main Street glows with lights, seasonal storefronts, and community events like the Port Holiday Stroll, packed with music, crafts, and treats from local businesses. Stop into Port Holiday Magic on November 29 for a bustling holiday market including costumed characters, trolley rides, shopping, and more.
The celebrations stretch across town, from the Landmark on Main Street, which hosts holiday concerts, children’s shows, and seasonal performances, to the Port Washington Chamber of Commerce Christmas Tree Lighting, a lively community gathering complete with caroling and hot cocoa. Families also love wandering the Bay Walk to catch the harbor lights twinkling on Manhasset Bay or visiting The Enchanted Home for local gifts and festive finds. And during early December, the Cow Neck Peninsula Historical Society runs special holiday-themed tours that add a dose of coastal history to your visit.
Oyster Bay, NY — Historic Cheer, Mansion Lights, and Coastal Festivities
Oyster Bay blends history and holiday spirit seamlessly. At Planting Fields Arboretum, the annual Holiday at the Mansions event fills Coe Hall with festive decorations, live music, seasonal tours, and outdoor light displays across the grounds. In town, the Oyster Bay Tree Lighting draws crowds each year, complete with carolers and hot cocoa stations. Families love touring Sagamore Hill, Theodore Roosevelt’s home, which adds seasonal decor and storytelling programs in December. Wander over to Southdown Coffee for a warm drink, then stroll through the quaint downtown to browse local shops and historic buildings decked out for the season.
Sea Cliff, NY — Vintage Holiday Charm on the Cliffs
Sea Cliff does the holidays with old-fashioned style. The village’s annual Holiday Tree Lighting in Clifton Park draws locals for carols, cocoa, and the lighting of the towering evergreen overlooking the harbor. Another local favorite: the annual Scrooge Stroll, which steps off from Centennial Garden. This roving retelling of A Christmas Carol brings Dickens’ classic to life through live narration and festive neighborhood stops. It’s a beloved community tradition, and a magical experience for all ages.
When you’re done, stroll down Sea Cliff Avenue to browse local shops, grab a warm drink from Dessertino or Campground Craft Beer & Coffee before calling it a day.
Huntington, NY — A Lively, Festive Main Street With Big Holiday Energy
Huntington turns into a full-on holiday hub each December, with its vibrant downtown glowing under rows of twinkling lights. Wall Street and Main Street come alive thanks to the annual Huntington Holiday Spectacular, a month-long outdoor festival featuring a massive illuminated tree, light displays, music, food pop-ups, and family-friendly activities. The town’s restaurants and cafés spill out onto the sidewalks with seasonal specials, and the whole area buzzes with that unmistakable holiday energy.
Make time for the Northport–Huntington Ice Rink at Heckscher Park, where families skate under the lights surrounded by snow-dusted trees, or slide over to The Paramount for a holiday concert or comedy show. The legendary venue’s December calendar is always packed. Shoppers can wander into beloved local spots like Book Revue’s successor The Next Chapter, and the many independent boutiques dotted throughout the village.
For a cozier moment, stroll through Heckscher Park to see the illuminated pathways and festive décor, or warm up with a seasonal latte at Southdown Coffee before grabbing dinner at favorites like Besito or Little Vincent’s, known for its “cold cheese” slice – a local rite of passage.
Whether you’re exploring for fun or thinking about a future move, these holiday towns in the NYC suburbs offer a festive, low-pressure way to get a feel for different communities.
For more insights, visit Suburban Jungle’s New York City suburbs section and the New York City blog page on our website.
Ready to get out there and start exploring holiday towns in the NYC suburbs? Schedule your free initial strategy call today.
