Cross-Border Hop: 10 Historic and Active Weekend Getaways in Upstate New York

The city of Hudson perhaps best embodies the wave of urban revitalization that has swept over the Hudson Valley in recent years. Artisan run boutique shops – like Lili & Loo with handcrafted home-goods galore – and farm-to-table eateries line the city’s main drag, Warren Street. Foodies or couples looking to celebrate a special occasion should snag a dinner reservation at the city’s acclaimed restaurant, Fish & Game. The James Beard Award-winning eatery serves an innovative, seasonal tasting menu with ingredients sourced from local Hudson Valley farms.

Beyond the charming downtown, Hudson lies in one of the most scenic spots along the Hudson River. Explore the bucolic hillsides, venture out for a hike, or check out the nearby Thomas Cole National Historic Site and learn about one of America’s first and most influential landscape painters.

Outdoors lovers flock to Ithaca, New York for all four seasons. The city’s location at the base of Cayuga Lake makes it an ideal place for exploring the entire Finger Lakes Region. In the warmer months, get out on the water for boating, fishing, and kayaking, or stay on land and sip your way around the Cayuga Lake Lake Wine Trail. Come winter, you can snowshoe and cross-country ski at the Cayuga Nature Center or tie up those laces to skate around the ice rink near Rice Hill.

In 1777, Kingston was named the first state capital of New York. While it no longer holds that title, Kingston is still one of the oldest cities in the state and one of the best destinations for a weekend getaway in Upstate New York.

Diego’s is one of the tastiest restaurants in all of the Hudson Valley, making finger-licking good tacos and other savoury Mexican food. Run by a husband and wife team, Diego’s serves outstanding Mexican street corn, tacos and margaritas. It’s worth the drive to Kingston alone.

Diego’s is ideal for lunch, but for dinner try to snag a table on the patio at Boitson’s. Start with an order of their famous Buffalo Cauliflower. (It tastes just like chicken wings.)

From May to November, Kingston has a great Saturday Farmer’s Market. Local vendors set up stalls to sell homemade soups, freshly-fermented kimchi, ginger tonics, and gorgeous blooms.

Just over five hours north of busy New York City, Lake Placid is an oasis of outdoor activities and relaxation. Lake Placid has twice hosted the Winter Olympics, and you can visit the sites where those world-class athletes competed and see how you compare.

Outdoor enthusiasts will love all the activities available in the heart of the Adirondacks. Do your best figure skating impression at the Olympic Oval, the same ice rink where Olympians speed-skaters competed during the 1932 and 1980 games. Hit the slopes at White Face Mountain, the fifth tallest peak in the country. Featuring the largest vertical drop in the East (3,430 feet!) and 87 trails, Whiteface Mountain presents skiers with challenging slopes and long, fun runs.

At the ski jump used for the 1980 Olympics, anyone with acrophobia may want to confront his or her fear. While you can’t actually ski there, the chair-lift ride up remains quite nerve-wracking. At the end of the tall lift, you’ll ride an elevator up even higher to the top of the jump to take in the view from the athletes’ vantage point. The panorama shot you get of the Adirondacks all around is pretty unbeatable.

At the Ausable Chasm, an expansive sandstone gorge, outdoor lovers can bike, raft, repel, tube, and rock climb – all while enjoying the stunning views. In the colder months, the tour includes snowshoes or ice cleats and you’ll see the frozen Ausable River, amazing ice and rock formations, and the chasm blanketed in powder. Hit the Adirondack Coast Wine Trail to tour the vineyards and sample some local flights – sure to warm you up from the inside out.

If you’re thinking of heading to Niagara Falls, ON, why not pop over the river to Buffalo, New York? The city, built on the shores of Lake Erie, is the second-largest in New York, and is known as an ideal destination for families and sports fans. Both the Buffalo Bills NFL football team and the Buffalo Sabres NHL hockey team call the city home, so sports fans are sure to be entertained fall through spring.

If you don’t have tickets (or don’t want to brave the cold), head to one of the great sports bars in town. The Anchor Bar has world-famous wings, while (716) Food & Sport is more of a luxury sports-watching experience with 76 state-of-the-art screens including a 38-foot video screen above the bar. For those looking for a fun weekend brunch experience, look no further than Trattoria Aroma. The upscale eatery in downtown Buffalo serves modern Italian fare and has an impressive Bloody Mary list on the weekends.

Year round, you can take in the work of famed American architect Frank Lloyd Wright. The Darwin Martin House, a Prairie school style estate, or the Wright Filling Station, a posthumously completed gas station designed by Wright in the 1920’s, are both great examples of Wright’s talent.

Saratoga Springs lies in the heart of the Hudson Valley. With a deep history of horse racing that dates back to the mid-1800s, the town has long made a name for itself for having a fun social scene with speakeasies and music clubs galore.

Set in the shadows of the Adirondack Mountains, you can spend your days watching a race, enjoying a polo match or hit the slot machines at the Saratoga Casino Hotel. To make the destination even more appealing, there are said to be 20 natural hot springs in the area. Over the years, the hot springs reputation has allowed the town to grow into a full-fledged spa destination. For an invigorating hydrotherapy experience, head to the Roosevelt Inn and Spa, where they boast a whopping 42 treatment rooms.

New Paltz is a wonderful town to visit for a relaxing, outdoor-oriented weekend getaway. For those thinking of making it to New York City, it’s less than a two-hour drive short of Manhattan. Start with a morning hike along one of the best trails in the state, the Lemon Squeeze. The trail begins at the Mohonk Mountain House and offers everything from fun rock maneuvering to incredible valley views. You can choose to undertake different sections of the trail depending on your desired hike intensity, and it’s safe for kids so long as parents are there, too. The full trail takes around four hours, while the shorter version takes one hour and is more of a rock scramble comprised of a fun mix of easy and adventurous terrain.

Following the exhilarating hike, a hearty lunch will definitely be needed. We suggest grabbing a sandwich (get the Santa Cruz) from the Main Street Bistro, a local’s favourite. Take your meal to go and enjoy a leisurely picnic by Lake Mohonk in the Mohonk Preserve.

The best way to cap off your day in New Paltz is to swing by Robibero Family Vineyards for a glass of Hudson Valley wine. Tastings are US$12 per person and the family-friendly winery has a big fire pit and plenty of space for friends and family to gather.

Albany is the state capital and one of the oldest surviving settlements of the original 13 colonies. Suffice to say, there’s plenty of history to soak in here not to mention the city’s renowned art and architecture.

In the downtown area, the pièce de résistance is Empire State Plaza. Here you’ll find an underground shopping mall filled with public art installations. Above ground, you can’t miss The Egg. The performing arts venue is home to two theatres and has become one of the most iconic landmarks in Albany.

Beacon’s location in the Southern Hudson Valley and accessibility by train make it an ideal destination for New York City dwellers in particular. However, its vibrant art scene and excellent hiking trails attract visitors from all over the state. Wake up early to hike the Mt. Beacon trail and catch a magnificent sunrise at the top.

For an afternoon activity, Dia:Beacon cannot be missed. Known as the “daylight museum”’ for its huge skylights above and housed in what used to be an old Nabisco factory, the acclaimed museum showcases an array of contemporary artwork.