Detailed Hudson Valley Weekend Road Trip Itinerary (2 hours from NYC)

If you’re looking for the perfect weekend getaway from NYC, the Hudson Valley should be at the top of your list. Just about two hours north, this region is packed with charming small towns, farm-to-table dining, vintage shops, scenic hikes, and hidden gems that make every stop feel like a mini adventure. Whether you’re a foodie, a thrifter, or just looking to escape the city for some fresh air and picturesque streets, this detailed Hudson Valley weekend road trip itinerary & travel guide will guide you through the best spots — from Kingston to Woodstock, Hudson, and beyond. Get ready to explore, eat, shop, and soak in the beauty of one of New York’s most magical regions.

First stop: Kingston

Food & Coffee:

Rough Draft book store & coffee
Deisings Bakery – classic pastries and baked goods
Village Coffee & Refillery – coffee and sustainable goodies
Rosie General – breakfast & to-go snacks
Salt Box – drinks & apps
Eliza Bistro – casual dining

Shopping & Thrift:

Capital Vintage
Red Owl Collective
Lovefield Vintage
Black Swan – vintage/thrift
Rewind Kingston – thrift
Everywhere Shop

Activities:

Tourist Train Ride – fun scenic intro to Kingston
People’s Place & Capital Vintage – antiques & collectibles
Rose Hill Farm for apple picking – 25 minutes away from downtown Kingston
Rhinebeck – 15 minute drive from Kingston – go to boutiques and historic town center & stop for a scenic view along the river at Rhinecliff

Hotels:

Hotel Kinsley

Phoenicia Diner

Retro Farm-to-Table Charm. Phoenicia Diner, a beloved retro roadside spot that’s been serving locals and travelers since the 1980s. With its classic diner vibe, indoor and outdoor seating, and even a vintage Airstream out front, it’s the perfect place to enjoy breakfast any time of day. Everything on the menu is farm-to-table, and if you’re like me and could eat breakfast for every meal, you’ll fall in love with their hearty classics. Whether you’re fueling up for a day of exploring Kingston or the surrounding Catskills, Phoenicia Diner is a must-stop for both the food and the nostalgia.

Woodstock

Food & Coffee:

Moonrise Bagels – stuffed bagels
Gemela – brunch & matcha
Bread Alone – sandwiches and baked goods
Goodnight – dinner
Small Talk – cocktails
Silvia – farm-to-table dining

Shopping & Thrift:

Tinker Street & Mill Hill Road – vintage shops
Candlestock – artistic, dripping candles
Gravity Vintage on Lotus Lane

Hotels:

Hudson

Food & Coffee:

Banque – chic bistro in a converted bank, pastries, gelato, coffee, craft cocktails
The Maker for coffee at their cafe, lunch or dinner at one of their restaurants, drinks at their lounge
WYLDE coffee & matcha shop
Kitty’s – indoor & outdoor seating – known for their breakfast

Shopping & Boutiques:

Made Hudson – local artisan goods
Warren Street – boutiques & antique stores
The Secret Gardener for plant lovers

Activities & Sights:

- Crimson Leaf Alpaca Farm
- Olana Historic House – photography and architecture
- Book a Hudson Valley Wine Tour – NY’s only sommelier guided wine tour
- Stroll the Henry Hudson Riverfront
- Go to Catskill Mountains
- Visit the Omi Sculpture Park

Hotels:

Wildflower Farms – voted NY’s #1 resort in 2025
The Maker Hotel– 11 beautiful guest rooms that are each uniquely decorated, has a cafe, restaurant, lounge, and pool.
The Amelia– 19th century Queen Anne-Style house with 8 rooms.
The Wick– housed in a former 18th century candle factory
Rivertown Lodge
Hudson B&B
The Hudson Whaler
Pocketbook Hotel & Baths
This is the Airbnb that I stayed in – it’s located in Athens which is just a short 10-15 minute drive from Hudson.

Catskills Area

10 minute drive from Hudson.

Food & Drinks:

Hemlock in Catskill– drinks in a cozy bar downtown
Phōs – Greek restaurant downtown Catskill
Bartlett House (in Ghent) – charming café and bakery set within a historic railroad hotel dating back to the 1800s.

Shopping & Thrift:

Pay It Forward Thrift Shop – unique finds

Hotels:

Other Nearby Stops Near The Hudson Valley

Ghent – 20 minute drive from Hudson – charming small town vibes
Kinderhook – small-town charm (20 minutes north of Ghent)
Saugerties – local shopping & dining (about 20 minutes south of Catskill)
Troy – farmers market on Saturdays and historic downtown streets
Flea Market (East Durham) – weekend treasure hunting & local finds
Chatham – picturesque small town perfect for a stroll
Tivoli – scenic riverside town with galleries and shops
New Paltz – great food, local culture, and small-town charm
Rose Hill Farm (Red Hook) – apple picking and farm fun
Wright’s Farm – outdoor farm fun
Minnewaska State Park Preserve
Peekskill Fall Foliage River Cruise

There’s also a ton of really fun Airbnb experiences in the area where locals take you horseback riding in the Catskill Mountains, interact with friendly farm animals, hugs & hike with rescue goats, hike the falls, cruise Twin Lakes, paint, meditate, stained glass classes, tie dye, yoga & so much more.

Tips for Your Hudson Valley Weekend Trip

Best Time to Go: Fall for foliage, spring for blooms, summer for sunny days
What to Pack: Comfortable walking shoes, jacket, camera, reusable bags for vintage finds
Must-Try Foods: Stuffed bagels at Moonrise, pastries at Banque, farm-to-table at Phoenicia Diner

How to Get There

The Hudson Valley is just about two hours from NYC, making it the perfect weekend escape. The easiest and most flexible way to explore the region is to rent a car — this lets you hop between towns like Kingston, Woodstock, Hudson, and Rhinebeck at your own pace, and discover hidden gems off the beaten path. I recommend booking through Discover Cars because they compare hundreds of local rental companies to find you the best price – and you can lock in your booking with free cancellation. Check their latest deals by clicking here.

If you prefer not to drive, Amtrak offers service from Penn Station in Manhattan to several Hudson Valley towns, including Hudson, Rhinecliff, and Poughkeepsie. The ride takes roughly 2 to 2.5 hours, depending on your destination, and offers scenic views of the Hudson River along the way. Once you arrive, you can grab a taxi, rideshare, or rent a local car to explore nearby towns. Whether you drive or ride, the journey north sets the tone for a perfect weekend getaway.

To purchase Amtrak tickets, visit the Amtrak website or use the Amtrak Fare Finder to find the best deals. Tickets for one-way trips from NYC to Hudson typically range from $35 to $66, depending on the time of booking and travel date. For the most up-to-date schedules and ticket availability, check the Amtrak Train Schedules & Timetables page.