Winter on Long Island offers a magical mix of cozy, romantic settings and exciting activities, perfect for couples looking to create lasting memories. Whether you're snuggling by the fire or exploring a winter wonderland, these ideas are sure to spark romance and adventure.
Fireside Dining and Drinks
Set the mood with an intimate dinner or drinks by a roaring fire.
Where to Go:
Prime: An American Kitchen & Bar in Huntington offers waterfront dining with a cozy fireplace and an exceptional menu.
The Shed in West Sayville is perfect for rustic charm and comfort food.
Jonathan’s Ristorante in Huntington Village combines upscale Italian cuisine with a warm, romantic ambiance.
Pair It With: A stroll through Huntington Village’s holiday lights or a stop by Kerber’s Farm for a dessert pie to share later.
Bonus Idea: Extend the evening with a romantic drive along Route 25A, known for its scenic beauty and historic charm.
Ice Skating Adventures
Embrace the winter chill with a fun and romantic ice-skating date.
Where to Go:
Mitchell Park Ice Rink in Greenport offers scenic views and a classic small-town vibe.
Christopher Morley Park Ice Rink in Roslyn provides an outdoor skating experience close to cozy cafés.
The Rinx at Hidden Pond Park in Hauppauge features both indoor and outdoor rinks for all-weather fun.
Pair It With: Hot chocolate and pastries from Blue Duck Bakery in Greenport or a warm bowl of soup at a nearby eatery.
Bonus Idea: Try skating at night for a more magical atmosphere with twinkling lights.
Wine and Spirits Tasting
Long Island’s wineries and distilleries are just as enchanting in winter.
Where to Go:
Bedell Cellars and Kontokosta Winery on the North Fork offer cozy tasting rooms with mulled wine and crackling fireplaces.
Long Island Spirits in Baiting Hollow serves artisanal spirits, perfect for a whiskey-tasting date.
Lenz Winery hosts intimate tastings in a rustic, barn-style setting.
Pair It With: Stop at a local farm stand like Briermere Farms for seasonal pies or fresh preserves to take home.
Bonus Idea: Plan your visit around sunset for breathtaking vineyard views.
Explore Nature’s Winter Beauty
Take in Long Island’s scenic landscapes blanketed in snow.
Where to Go:
Mashomack Preserve on Shelter Island offers serene hiking trails through pristine winter landscapes.
Caleb Smith State Park in Smithtown is a peaceful spot for a quiet walk and winter wildlife spotting.
Avalon Park and Preserve in Stony Brook is ideal for a snowy stroll or nature photography.
Pair It With: Pack a thermos of hot cocoa and some cookies for a cozy break on the trail.
Bonus Idea: Try snowshoeing or cross-country skiing at Bethpage State Park if there’s fresh snowfall.
Winter Workshops and Classes
Bond over learning something new and creative.
Where to Go:
Take a pottery class at The Clay Place in Port Jefferson, where you can create a keepsake together.
Sign up for a cooking class at Sur La Table in Manhasset and learn to make a romantic dinner at home.
Try candle-making at Little Miss Sew It All in Huntington for a hands-on experience.
Pair It With: A coffee date afterward to chat about your creations at Toast Coffeehouse in Port Jefferson.
Bonus Idea: Gift each other your finished creations as a sentimental token of the date.
Take in a Show or Concert
Enjoy a cultural experience with live performances and entertainment.
Where to Go:
Catch a live show at The Paramount in Huntington, known for its intimate setting and popular acts.
Enjoy a Broadway-caliber production at The Gateway Playhouse in Bellport.
See a film at Sag Harbor Cinema, which combines art-house charm with historic elegance.
Pair It With: Dinner and drinks at nearby restaurants like Swallow Restaurant in Huntington or The Bellport for a more intimate setting.
Bonus Idea: Choose a show that aligns with your partner’s interests to make the night extra special.
Holiday Light Displays and Markets
Enjoy the sparkle and cheer of winter festivities.
Where to Go:
Drive through the Smith Point Light Show in Shirley or the Shimmering Solstice at Old Westbury Gardens for enchanting displays.
Stroll through the Greenport Winter Village for lights, local crafts, and seasonal treats.
Explore the Port Jefferson Dickens Festival in December for a step back in time with Victorian carolers and holiday markets.
Pair It With: A stop for mulled cider and freshly baked cookies at a local café.
Bonus Idea: Capture holiday-themed photos for your social media feed or holiday cards.
Romantic Beach Walks and Picnics
Winter beaches offer quiet, scenic beauty that’s perfect for couples.
Where to Go:
Visit Cupsogue Beach County Park in Westhampton for breathtaking winter waves.
Explore the rugged coastline at Montauk Point State Park, where the lighthouse creates a dramatic backdrop.
Stroll along the sands of Long Beach for peaceful ocean views.
Pair It With: A picnic with thermoses of soup, warm blankets, and pastries from a local bakery like Marie Eiffel Market.
Bonus Idea: End the day with a bonfire if permitted, for a truly magical finish.
Winter Getaways
Make your date a full weekend with a winter retreat.
Where to Go:
Book a stay at Oheka Castle in Huntington for a fairytale experience.
Escape to Gurney’s Montauk Resort for oceanfront luxury with spa amenities.
Enjoy the boutique charm of Sound View Greenport with panoramic views of the Long Island Sound.
Pair It With: Spa treatments, in-room dining, and quiet time to relax together.
Bonus Idea: Capture dreamy photos of your getaway spot to share the romantic vibes.
Sledding and Snow Play
Release your inner child with some fun in the snow.
Where to Go:
Bethpage State Park and Belmont Lake State Park offer perfect hills for sledding.
Build a snowman or have a playful snowball fight at Heckscher State Park.
Pair It With: A stop at a nearby café for warming drinks and treats after your outdoor adventure.
Bonus Idea: Share a candid video of your snow-filled fun to capture the playful energy of the day.
Make Your Winter Magical
Whether you’re skating under the stars, sipping mulled wine, or walking hand-in-hand through snowy trails, Long Island offers endless possibilities for unforgettable winter dates. Which one will you try first? Share your adventures with us @bucketlistli and inspire others to embrace the season!