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Elevate Your Extra Day: A Cannabis Guide to Long Wintry Weekends in NYC

Mar 2, 2026

Winter in New York doesn’t have to be one long, cold stretch. It’s best when broken up into long weekends. By breaking the winter up with unique weekend activities, you can get the most out of the season balanced with much-needed pauses and resets.

Whether you decide to leave New York to break up the winter or stay put and lean into it, you’re bound to have a good time with a little planning. We’ve put together several long weekend itinerary options so you can live it up this winter.

Long weekends without leaving the City

Spending a long weekend in NYC can be just as exciting as taking off. In fact, not leaving is the escape. Many New Yorkers love mini staycations to break up the wintertime without any excruciating travel logistics. Plus, it’s a great way to appreciate the city and all its familiarity, while still spicing things up.

You can take a NYC staycation in any direction, from hotel stays to reservations at that restaurant you’ve been meaning to try. Visit a museum or go on a long, quiet stroll through to see the city in a new light. Don’t forget the addition of some high-end cannabis, especially if you want to see the city in a new and exciting way.

Need some inspiration?

Book a stay at the Aman New York and hit the swimming pool, spa, and pilates studio. Or stay at the William Vale, where you can make use of the Nordic-inspired outdoor saunas and hot tubs.

For dinner, hit Eataly for a dreamy, Italian meal that satisfies all your senses. Or visit Pinch Chinese, where you can enjoy a romantic setting and amazing dishes.

A snowy path in Hudson Valley in the winter, with blue skies above

Long weekends a short train ride away

Want a bit more of an escape? Hit a Hudson Valley reset. With easy access by train, it’s the perfect destination for a quick escape without too much planning.

All you need to do for a fabulous long weekend trip is book a cozy cabin stay. Enjoy the world of small-town dining, cozy bookstores, and treasures abound at antique stores.

Feeling especially motivated? Plan out some cold-weather hikes for a magical experience that feels far removed from city life.

If you’re looking to leave the hustle and bustle of Manhattan for a long weekend trip, consider a Catskills cabin weekend. It’s a quiet, cozy way to enjoy a “nothing scheduled” go-with-the-flow weekend alone or with loved ones.

Start a crackling fire, open your book, and go for a frosty snow walk. Follow it up with some great cannabis products.

Long weekends that feel earned

Looking for a bit more of an escape this New York winter? We’ve got you covered with some fantastic long weekend trip ideas.

Montreal

First, hit Montreal for a winter city break. It’s a walkable, food-forward city that makes winter feel more exciting.

New Yorkers have long loved traveling to Montreal for an escape from life on the Upper East Side. From amazing restaurants and cafes to cozy winter festivals, spas, and museums, Montreal has it all.

Miami or Palm Beach

Need a little sunshine to break up the New York cold? You can’t go wrong with a trip to Miami or Palm Beach. It’s a short flight and easy trip that delivers much-needed sunshine, beaches, and plenty of pools. You can indulge in light social plans and wrap up your nights early by the pool, without any pressure.

Winter is also museum season in Miami, making it a great destination for those with an appetite for learning.

Charleston or Savannah

In between the winter wonderland of Montreal and the sunshine escape of Miami and Palm Beach lies a weekend trip to Charleston or Savannah. Indulge in the slow pace and charm of these cities, with their mild winters and walkable historic centers.

You can live the slow life for a weekend while enjoying the many great coffee shops, restaurants, and walkable destinations.

Find your rhythm in winter

However you choose to plan your long weekend itinerary, remember that winter works best with a series of gentle pauses. You don’t have to flee for the season, just break it up into fun, relaxing trips that invigorate your zest for life.

Our Upper East Side dispensary is here to help you make the most of your winter. We bring luxury New York cannabis to those who have a taste for the finer things in life. Stock up for your long weekend in NYC by stopping by Maryjane.

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