3 Classic Weekend Trip Upstate

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  • Yield: 1-5 hours
  • Serving: 2-3 days
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Like a slice of apple pie paired with a scoop of vanilla ice cream or an NYC hot dog topped with onion relish and a zig-zag of mustard, a classic weekend trip should be a tried-and-tested combination. A foolproof, easy-to-follow recipe that’s guaranteed to hit the mark, whatever your travel (or food) preference.

Similarly, these three ready-made weekend itineraries are packed with classic destinations and timeless activities. Take your pick between wine tasting in the Finger Lakes, a culture-packed stay in Hudson, or an outdoor adventure in the Catskills, and enjoy a classic weekend trip Upstate.

Essential Ingredients

A classic weekend trip requires the perfect mix of ingredients, carefully proportioned to give just the right amount of entertainment and relaxation. Make sure you add the following into the mix:

Characterful towns

Perched riverside or amid rolling hills, Upstate’s small towns each have their own unique character. Choose a basecamp with a vibe that matches your own, whether you favor heritage architecture and antique shopping, a buzzing live music scene, or a country retreat by the lakeside.

Outdoor Activities

From glimmering lakes to rugged mountains, Upstate NY is a paradise for outdoor enthusiasts. Weekend breaks are all about short hikes, mouth-watering views, and bitesize back-to-nature experiences, whether stand-up paddleboarding on the lake or zipping along mountain trails on a snowmobile.

Foodie favorites

Whether following the Upstate Eats food trail or snagging a table at an award-winning eatery, Upstate’s foodie scene easily rivals that of the state capital. Pepper your weekend with wine tasting tours and laid-back brunches, tuck into seasonal delicacies and street food favorites, or follow the locals to the best restaurant in town.

Boutique B&Bs

A short stay is an ideal time to splash out on the perfect accommodation. Cozy up around a roaring fire in a traditional inn, check into an Instagrammable design hotel, or opt for 5-star rest and relaxation at a luxury spa resort.

The Classic Weekend Trip Upstate: 3 Recipe Ideas
Serving size: a 2-3 day weekend
Courses: Finger Lakes, Catskills, Hudson
Cuisine: Weekenders, Wine lovers, Outdoors Adventurers
Cooking Notes: road trip, outdoor activities, boutique hotels, wine tasting, hiking, waterfalls, lakes, mountains, arts & culture


Weekend 1: Wine Tasting in the Finger Lakes

Drive time: about 5 hours from NYC.
The Finger Lakes are the classic ‘all-in-one’ Upstate NY destination with rugged gorges, lakeside beaches, and award-winning wineries on tap. Base yourself in Ithaca or Watkins Glen, and fill your weekend with wine tasting, hiking, and lakeside fun.

Must-do activities include a hike along the Gorge Trail in Watkins Glen State Park and a visit to Taughannock Falls , along with a scenic cruise around Seneca Lake. Or, rent a pedal boat, kayak, or stand-up paddleboard on Cayuga Lake.

The Seneca Lake and Cayuga Lake wine trails provide dozens of options for wine tasting–Belhurst Estate Winery and Chateau LaFayette Reneau are among the most popular, while Fox Run Vineyards also runs guided vineyard tours. Throw in a winery lunch and a lake-view room for the ultimate Finger Lakes getaway.

Classic stays:

Watkins Glen Harbor Hotel
16 North Franklin St. Watkins Glen, NY, 607-535-6116.
Deluxe rooms with panoramic lake views, right on the shore of Seneca Lake.

William Henry Miller Inn
303 N Aurora St, 14850, Ithaca, 607-256-4553.
Cozy inn accommodation in a grand 19 th-century manor in downtown Ithaca.

Classic Eats:

The Ginny lee @ Wagner Vineyards 9322 State Route 414, Lodi NY 14860, 607-582-6574.
Tuck into lunch with a lake view and pair it with the estate’s homemade wines and craft beers.

F.L.X Table 22 Linden Street, Geneva, NY 14456, 315-730-3083.
Gourmet gastronomy with a dinner party vibe.


Weekend 2: Back-to-Nature Retreat in the Catskills

Drive time: about 2.5 hours from NYC.
With over 700,000 acres of wilderness to explore, a classic Catskills weekend involves mountain hikes, scenic road trips, and plenty of fresh air. Pack your hiking boots, check into a swish mountain resort or a cabin in the woods, and fuel your explorations with hearty farm-to-table cuisine along the way.

Enjoy a brisk morning hike through the Minnewaska State Park Preserve, an idyllic spot to admire fall foliage, then head north to Woodstock or Bethel, where the bohemian spirit of the 1960’s festival still lives on. The view from Overlook Mountain in Woodstock is among the most memorable, but equally magnificent is Kaaterskill Falls, just a short drive north. Time to spare? Rent a mountain bike, go horseback riding, or pack a picnic and take a leisurely road trip along the Catskill Mountains Scenic Byway.

Classic stays:

The Roxbury
2258 County Highway 41, Roxbury, NY 12474, 607-323-8241.
Part lavish Catskills resort, part Alice in Wonderland-inspired design hotel.

Bellfire Meeker Hollow,
Roxbury, NY.
Instagram-worthy glampsites, including a birdhouse and tipi amid rambling woodlands.

Classic Eats:

The Farmhouse Project Hortonville, NY 12745.
Immersive dining experiences that take farm-fresh to a whole new level.

The Heron 40 Main Street, Narrowsburg, NY, 845-252-3333.
Narrowsburg’s most celebrated restaurant pairs farm-to-fork cuisine with river views.

Henning’s Local Cochecton Center, NY 12727, 845-252-3008.
Norwegian creativity meets all-American produce at one of the Catskills’ most popular farm-to-table restaurants.


Weekend 3: Small-Town Escape in Hudson

Drive time: about 2.5 hours from NYC.
Foodies, wine lovers, and antiques enthusiasts congregate in Hudson, the king of small-town pleasures. A classic weekend starts with brunch at one of Hudson’s beloved cafés (Home/Made gets our vote), followed by boutique-hopping along Warren Street. While away the afternoon hunting for antique finds, vintage pieces, and independent designer wares, then head down to Promenade Hill to watch the sunset over the Hudson River.

Staying out after sunset? Catch a gig at Helsinki Hudson, work through the NY state craft beer menu at the Hudson Brewing Company, or sojourn to The Maker lounge for cocktails. The following day, kick things off with a hilltop walk and a visit to the Olana State Historic Site, then set out to explore the Hudson Valley. The riverside towns of Kingston and Poughkeepsie are both under an hour drive away; alternatively, enjoy wine tasting at Tousey Winery or seasonal apple-picking and cider doughnuts at Rose Hill Farm .

Classic stays:

The Maker 302 Warren Street Hudson, NY 12534, 518 509 2620.
A bohemian spirit and literary inspirations reign at Hudson’s latest boutique stay.

Rivertown Lodge 731 Warren Street, Hudson, NY 12534, USA, 518-512-0954.
Boutique beds in a former 1920’s movie theater.

Classic Eats:

Lil’ Deb’s Oasis 747 Columbia Street, Hudson, NY 12534, (518) 828-4307.
Dive into Caribbean flavors and creative vibes at this Queer-run eatery – the most colorful spot in town.

Red Dot Restaurant 321 Warren Street, Hudson, NY, 518-828-3657.
Hudson’s longest-running restaurant is a perennial local favorite.

Breadfolks Bakery 322 Warren Street, Hudson, NY 12534, 518-660-3093.
Hudson’s most beloved bakery for all your morning coffee, pastry, and picnic needs.


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Tips & variations

  • Book ahead: whether it’s hotels, flights, or tours, weekends tend to book up fast, especially over holiday weekends. Last-minute getaways might sound romantic, but booking well in advance means you’ll secure the best rates and avoid disappointment.

  • Keep your itinerary flexible: advance planning is essential, but don’t plan every minute of your itinerary either. Leisurely brunches, boutique browsing, and spontaneous detours are all part of the fun.

  • Consider your transport options: many Upstate towns and cities connect to NYC and other U.S. cities by train and plane, and it’s worth looking around to find the quickest and most economical options. However, renting a car is still a smart idea unless you’re planning a resort stay.

  • Enjoy seasonal sightseeing: Upstate is good for a weekend break year-round, but be sure to make the most of seasonal activities. Fall foliage drives in NY state are among the best in the county, festivals are held around the Hudson Valley throughout summer, and winter is ski season in the Catskills.


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