Ultimate Upstate NY Road Trip - Hiking, Gorges, Waterfalls

Jacqueline Krawiecki - (jkrow)
Itinerary created by
Jacqueline Krawiecki
What you’ll do

This road trip through Upstate New York is the ideal blend of natural beauty, cultural richness, outdoor adventure, and historical interest. It'll lead you off the beaten path to experience New York's charm, which goes far beyond the bright lights of its famous city.

From the towering peaks of the Adirondacks to the shimmering waters of the Finger Lakes, this expertly designed 9-day itinerary will guide you through the very heart of New York State, unveiling diverse landscapes, a wealth of cultural experiences, and plenty of opportunity to mix adventure with relaxation.

KNOW BEFORE YOU GO

  1. Nearest airport: John F. Kennedy (JFK) airport in NYC or Albany International Airport (ALB) in Albany

  2. Best time to go: In general, this road trip is best done between mid June - mid October for the best weather. Note that some things on this itinerary are seasonal and weather dependent, so double check updated information before you go.

  • May - July are the best time to visit for waterfalls.

  • Mid-June - early Sept is best for swimming, camping, and hiking

  • October is the best time to visit for fall foliage. Here's my guide on when/where to see the best fall colors in Upstate New York.

  • May - July is black fly season in the mountains. Black fly season typically lasts from mid-May to mid-July.

Read more on how to avoid/protect yourself from black flies here:

How to Survive Black Fly Season

  1. How to get around: You'll be doing a lotttt of driving over these 9 days, so you'll definitely need to rent a car to complete this itinerary!

Alternatively, you could rent a campervan through Outdoorsy and search for campsites as you go using The Dyrt app (available for iOS and Android).

**ITINERARY OVERVIEW **

  • Day 1: Catskill Mountains

  • Day 2-3: Finger Lakes Region

  • Day 4: Central New York to Southern Adirondacks and Old Forge

  • Day 5: Central Adirondacks to Lake Placid

  • Day 6: Keene Valley

  • Day 7: Lake Placid and Northern Adirondacks

  • Day 8: Lake George

  • Day 9: Lake George to Hudson Valley

  • Total miles to drive over 9 days: 1110 miles (1770.3 km)

  • Total drive time over 9 days: 23 hours 24 minutes

Your journey begins in the Catskill Mountains and visit historic towns like Woodstock, with their vibrant arts scene and intriguing history.

From there, your path leads to the awe-inspiring Finger Lakes region. Known for their impressive gorges and scenic waterfalls, the Finger Lakes are also a paradise for wine lovers, with a multitude of vineyards dotting the rolling landscape.

Next, you'll ascend into the high peaks of the Adirondacks, an area rich with outdoor activities. Whether you're exploring a quaint mountain town like Lake Placid, hiking through verdant forests, or discovering the local wildlife, the Adirondacks are sure to leave you with memories to cherish.

Finally, unwind alongside the tranquil shores of Lake George. Here, days are filled with leisurely strolls through charming local shops, waterfalls, and evenings spent enjoying the peaceful lake views.

Stop 1: Kaaterskill Falls - Kick off your Upstate New York road trip with a visit to Kaaterskill Falls in the Catskill Mountains, one of the highest waterfalls in the state. The hike to the bottom of the falls can be steep, but the stunning natural beauty makes it the perfect start to your journey.

If you decide that you won't feel like hiking, there's a viewing platform only 0.5 miles from the trailhead off Laurel House Road. From there, you'll have a great view of the falls and the surrounding valley.

  • Stop 2: Woodstock - Next, back track just a little bit to the town of Woodstock and spend some time exploring Tinker Street. As the main street in town, it's home to a variety of unique shops and art galleries that capture the local spirit.

  • Stop 3: Que Lo Que - When you get hungry, stop by Que Lo Que, a local favorite known for its diverse Caribbean-inspired menu. Unforunately, they don't take reservations and the restaurant is pretty small. You'll want to get there before the dinner rush if you want a table. Otherwise, you can grab a seat at the bar.

If Que Lo Que is full, or if you're just craving something different, Sharkie's (Italian food) and The Bear Cantina (Mexican food) are also good!

  • Stop 4: Woodstock Way Hotel - Located right in town and beside a beautiful waterfall, the hotel combines modern comfort with rustic charm for a relaxing stay.

The hotels in this itinerary are hand picked just for you, but feel free to browse for a different one that best suits your price point and available dates

1

Kaaterskill Falls via Laurel House Road
Kaaterskill Falls via Laurel House Road
Tallest waterfall in Upstate New York
Category
Waterfall

31.9 km (19.8 mi)

35 min

2

Tinker Street, Woodstock
Tinker Street, Woodstock
Shops, restaurants, and art galleries in Woodstock
Category
Shop
Est. Price
$$

1.5 km (1 mi)

1 min

3

Que Lo Que
Que Lo Que
Latin American food with a twist
Category
Restaurant

205 m (0.1 mi)

1 min

4

Choose the option that fits you the best

Woodstock Way Hotel
Woodstock Way Hotel
Contemporary hotel in the heart of Woodstock
Category
Hotel

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