The Best Cold-Weather Activities in 10 Iconic “Summer” Towns

It’s time to kick off your sandals and strap on your skates for your off-season Hamptons getaway. If you’re visiting during a particularly frigid period (and come equipped with your own set of skates) Town Pond and Hook Pond may be sufficiently frozen over so that you can feel as if you’re skating inside a literal Christmas card. Or, you can try an ice skating rink like Buck Skill Winter Park, which touts the only NHL-regulation size rink in the Hamptons (as well as a clubhouse where skaters can indulge in a little après-skate European hot chocolate).

Orlando may be home to theme park friendly year-round, but something magical happens between October and June in the Sunshine State—this is when oranges (along with other citrus fruits) are officially in season. Indulge in experiencing an orange when it’s at its absolute freshest by visiting a produce stand or you can find your way to a grove where you can take a tour and potentially have the chance to sample an orange straight from the tree itself.

Springtime may be the quintessential period for viewing some flowers brilliantly in bloom, don’t count out the cooler months when it comes to taking in a floral display. Brookgreen Gardens plays host to many flowers that thrive when temperatures drop. And, if your visit is timed during the holiday season, you’ll get a chance to experience their Nights of a Thousand Candles event, during which the gardens are lit by the glow of nearly 3,000 candles.

While a lot of cold-weather options in beach towns take place farther inland, one of the more exciting activities visitors can partake in at the Outer Banks takes place right on the shore. Between October 1 and April 30, you can drive directly on Kill Devil Hills and Nags Head Beaches (just make sure you get the required permit ahead of time). So if the idea of long walks on the beach sounds more taxing than you’d like, you can still have a leisurely beach experience (with the added benefit of being in a climate-controlled space).

By the standards of most other parts of the country, winter and fall in Santa Barbara may not really rise to the widely-accepted definition of “cold-weather.” But it does get, by SoCal standards, certifiably nippy. And while the day-trippers from nearby Los Angeles may taper off, someone else moves in. Migrating gray whales, to be precise. From November through April, you’ll have a good chance to see these magnificent beasts over the course of a whale watching tour. There’s also a possibility of seeing orca and minke whales during this period.

To be fair, there isn’t exactly a bad time to go fishing during a trip to the Lake of the Ozarks. When temperatures drop, it becomes an excellent time to catch bass and crappie. So even if you’re not the most experienced angler, the wintertime is actually a great time to work on your bragging rights. Not to mention, you’ll still have that stunning Ozarks scenery to keep you company while you wait to reel in your catches.

A cold-weather trip to Maine may evoke images of zipping down snow-laden mountainsides, but if the need for speed doesn’t figure in your vacation hierarchy, you can enjoy the cross country version of the sport during a trip to Kennebunkport. Check out spots like Harris Farm where everyone from beginners to experts can explore acres of farmland on their trails. If you’re feeling competitive, the Wells Reserve at Laudholm encourages visitors to log their distance crossed on the trail in a nod to the traditional løpet style race.

Saugatuck makes for a great spot for anyone hoping to bask in some wondrous fall foliage. If you’re looking for a unique twist on the leaf-peeping excursion, consider taking a boat tour that will allow you to experience the views from a unique vantage point. But if you’re looking to stretch your legs a little more, there are plenty of good places to go for a stroll (like along Oval Beach). If you’re looking for something just a little bit more challenging still, head to Mt. Baldhead, a one-mile loop trail that rewards hikers with stunning views.

Cannon Beach is an absolutely beautiful place at any time of year, but there’s something special that happens during the cooler months that you’re not as likely to experience during the height of summer. Roosevelt elk are commonly seen in the area after the busy season. These majestic creatures tend to be found in the early morning or around dusk grazing in meadows of Ecola State Park. Though they make for a remarkably peaceful sight remember to keep a reasonable distance, as they are wild animals and bull Roosevelt elk can weigh up to 1,200 pounds and come equipped with an impressive set of antlers.

Galveston in the fall and winter makes for an excellent birding locale as the weather is more mild and fewer crowds crowding their way through town. Galveston Island State Park makes for a good base of any birding operations, as it offers the opportunity to see a myriad of birds, including peregrine falcons which have been known to visit the park’s beaches.