Nestled in the heart of the Hudson Valley, Pawling, NY, is a picturesque town that offers a perfect blend of natural beauty and small-town charm. Known for its lush landscapes and historic sites, Pawling is a haven for outdoor enthusiasts and history buffs alike. With its roots dating back to the 18th century, the town boasts a rich history that is reflected in its well-preserved architecture and cultural landmarks.

From the scenic trails of the Appalachian Mountains to the tranquil waters of the Great Swamp, Pawling is a paradise for nature lovers. The town's vibrant community and local businesses offer a warm welcome to visitors, with a variety of dining options that showcase the region's farm-to-table cuisine. Whether you're exploring the historic Main Street or enjoying a leisurely hike, Pawling promises a delightful escape from the hustle and bustle of city life.

As you plan your visit, keep in mind that Pawling is easily accessible by train from New York City, making it an ideal destination for a relaxing getaway. With a range of accommodations available, from cozy bed-and-breakfasts to charming vacation rentals, you'll find the perfect place to unwind after a day of exploration. Get ready to discover the hidden gems of Pawling, NY, with this detailed 7-day itinerary.

Pawling

Day 1: Arrival and Evening Stroll

Afternoon: Arrive in Pawling and check into your accommodation. Consider staying at a cozy rental through VRBO or a comfortable hotel via Hotels.com.

Evening: Take a leisurely stroll along Pawling's historic Main Street. Enjoy dinner at McKinney & Doyle, a local favorite known for its hearty American fare and welcoming atmosphere. Don't miss their famous homemade pies for dessert.

Day 2: Exploring Nature and Local Flavors

Morning: Start your day with a hearty breakfast at the Pawling Bread Co., where you can savor freshly baked pastries and artisanal coffee.

Afternoon: Head to the Appalachian Trail for a scenic hike. The trail offers breathtaking views of the Hudson Valley and is a must-visit for outdoor enthusiasts.

Evening: After a day of hiking, unwind with dinner at Vinny's Deli & Pasta, a beloved local spot offering authentic Italian dishes. Try their homemade pasta for a true taste of Italy in Pawling.

Day 3: Cultural and Historical Exploration

Morning: Visit the John Kane House, a historic site that played a role in the American Revolution. The museum offers fascinating insights into Pawling's past.

Afternoon: Enjoy lunch at the Front Street Gallery Café, where you can admire local artwork while savoring a delicious meal.

Evening: Attend a performance at the Pawling Concert Series, which features a variety of musical acts throughout the year. Check their schedule for upcoming events.

Day 4: Day Trip to the Great Swamp

Spend the day exploring the Great Swamp, one of New York's largest freshwater wetlands. Enjoy birdwatching, kayaking, or simply soaking in the serene surroundings. Pack a picnic lunch to enjoy amidst nature.

Day 5: Shopping and Relaxation

Morning: Browse the unique shops and boutiques on Main Street. From antiques to artisanal crafts, you're sure to find a special souvenir.

Afternoon: Treat yourself to a relaxing afternoon at the Pawling Yoga & Wellness Center. Join a yoga class or indulge in a soothing massage.

Evening: Dine at The Station Inn, a charming restaurant located in a historic train station. Their farm-to-table menu features seasonal ingredients and local flavors.

Day 6: Outdoor Adventures and Local Brews

Morning: Embark on a guided horseback riding tour at the Lucky Orphans Horse Rescue. Experience the beauty of Pawling's countryside from a unique perspective.

Afternoon: Visit the Daryl's House Club for lunch and live music. Founded by musician Daryl Hall, this venue offers a lively atmosphere and great food.

Evening: Sample local craft beers at the Pawling Tavern, a cozy pub with a friendly vibe. Pair your drink with their delicious pub fare for a perfect end to the day.

Day 7: Farewell to Pawling

Morning: Enjoy a leisurely breakfast at the Lakeside Park Café, overlooking the tranquil waters of Green Mountain Lake.

Afternoon: Before departing, take a final walk through Lakeside Park, where you can relax by the lake or explore the park's trails.

As your week in Pawling comes to an end, you'll leave with cherished memories of its natural beauty, rich history, and warm hospitality. Whether you were hiking the Appalachian Trail or savoring local cuisine, Pawling offers a unique and unforgettable experience.