A Perfect 2 Night Itinerary for New Paltz, NY

Welcome to New Paltz, NY—a funky, vibrant town tucked into the heart of the Hudson Valley. Known for its mountain views, creative spirit, and easy access to outdoor adventure, New Paltz is an ideal destination for a 3-day getaway.

As local experts, we’ve created the perfect 2-night/3-day New Paltz itinerary to help you experience the best of the area, from scenic hikes and charming downtown streets to farm cideries and unforgettable mountain sunsets.

Where to Stay in New Paltz, NY

One of the best parts of visiting New Paltz is the scenery. Nestled between the Hudson River and the Shawangunk Mountains, your home base should feel peaceful, scenic, and centrally located.

Watergrasshill Bed & Breakfast is an ideal place to stay in New Paltz, NY. This beautifully restored farmhouse blends rustic charm with modern comforts and sits on 15 acres of landscaped grounds with sweeping views of the Shawangunk Mountains. Guests enjoy thoughtfully designed rooms, tranquil outdoor spaces, and the quiet beauty of the Hudson Valley countryside—just minutes from town.

Each stay includes a from-scratch breakfast made with seasonal ingredients , served in the dining room or on the mountain-view patio when weather allows.

One of the most valuable perks of staying at Watergrasshill Bed & Breakfast? Your innkeeper. Owner and innkeeper Alana is a local expert who loves sharing personalized recommendations—from crowd-free hiking tips during peak season to the best spots for food, drink, and hidden gems.

A Perfect 2-Night / 3-Day New Paltz Itinerary (April–November)

Visiting New Paltz between April and November? This 2-night, 3-day itinerary is ideal for travelers who want a relaxed arrival day, one full adventure-packed day, and a slower final day to soak in the Hudson Valley before heading home.

Day One: Arrival & Settle In

Arrive in New Paltz and make your way to Watergrasshill Bed & Breakfast, your scenic home base for your stay. Take time to get settled into your guest room, wander the grounds, and enjoy views of the Shawangunk Mountains. After the drive, this first evening is all about slowing down and easing into Hudson Valley time.

Evening: Dinner & Mountain Views

Head out for a relaxed dinner at one of the many independently owned restaurants in New Paltz or nearby Gardiner.

Watergrasshill Dinner Picks: Pitanga North

After dinner, return to the inn to enjoy a quiet evening on the back patio with a glass of wine or cozy cup of tea as the sun sets behind the mountains. An early night sets the tone for a full day of exploring ahead.

Day Two: Mountains, Main Street & Sunset Views

Morning: Breakfast with a View

Start your first morning with a leisurely, from-scratch breakfast at Watergrasshill Bed & Breakfast. Take in the mountain views, sip your coffee, and fuel up for a day of exploring the outdoors.

Late Morning: Hiking at Minnewaska State Park

After breakfast, take a short drive into the mountains to Minnewaska State Park Preserve, one of the most iconic outdoor destinations in the region. With trails for all skill levels, Minnewaska offers waterfalls, crystal-clear lakes, dramatic cliffs, and panoramic views of the Hudson Valley—all in one park.

Afternoon: Downtown New Paltz

After your hike, head into downtown New Paltz. Stroll along Main Street and its lively side streets, browse eclectic boutiques, bookstores, and antique shops, and settle in for lunch at a local café.

Watergrasshill Lunch Pick: Lola’s Café

Mid-Afternoon: Nap or Farm Cidery Visit

Now it’s time to choose your own adventure:

• Return to your New Paltz bed and breakfast for an afternoon nap in your cozy guest room or relax in an outdoor hammock

• Or continue exploring with a visit to a local farm cidery or brewery

Within 12 miles of Watergrasshill Bed & Breakfast, you’ll find some of the Hudson Valley’s best cideries and breweries, including Kettleborough Cider House, Gardiner Brewing Company, Twin Star Orchards, Bad Seed Cider Co., and Locust Grove Brewing Co.

These destinations reflect the true spirit of the Hudson Valley—many are family-owned, agriculture-focused, and deeply connected to the land.

Watergrasshill Drink Pick: Honey Honey from Kettleborough Cider House

Evening: Dinner & Sunset Views

After your afternoon rest or farm brewery visit, freshen up back at your home base in New Paltz. Enjoy dinner in town at another locals favorite spot!

Watergrasshill Dinner Pick: The Ridge

Day Three: History, Scenic Drives & Slow Hudson Valley Moments

Morning: Breakfast & a Rail Trail Stroll

Begin your final morning with another from-scratch breakfast at Watergrasshill Bed & Breakfast. Before checking out, take advantage of direct access to the Wallkill Valley Rail Trail right from the property. A peaceful morning stroll along the trail is the perfect way to stretch your legs, enjoy fresh air, and savor the Hudson Valley scenery one last time.

Late Morning: Historic Huguenot Street

Head into town to explore Historic Huguenot Street, a National Historic Landmark featuring original stone houses and walking paths that tell the story of New Paltz’s early settlers. This is a great way to experience the town’s history while enjoying a gentle, walkable outing.

Afternoon: Scenic Drive or Farm Market Stop

Before heading home, enjoy a scenic drive through Gardiner and the surrounding countryside or stop at a local farm market to stock up on Hudson Valley goodies.

Watergrasshill Farm Pick: Wallkill View Farm Market

Plan Your New Paltz Getaway

New Paltz is an ideal destination for a 3-day Hudson Valley trip, offering a mix of outdoor adventure, small-town charm, and local food and drink. When you book your stay at Watergrasshill Bed & Breakfast, you’ll receive personalized recommendations from your innkeeper along with a curated guide to the best things to do throughout the Hudson Valley. Visiting in the winter: check our guide to a winter escape in the Hudson Valley.

We can’t wait to welcome you to New Paltz, NY.