Pawling, New York, is a charming town with lots to see and do. Nestled in the scenic Hudson Valley, it offers a mix of outdoor activities, local shops, and delicious dining options. Whether you are looking for a relaxing day in nature or an adventure in the town, Pawling has something for everyone.
In this guide, we will be highlighting some of the best things to do in Pawling. From hiking beautiful trails to enjoying fun events, there’s no shortage of exciting experiences. Get ready to uncover what makes Pawling a special place to visit or live!
Things to Do in Pawling NY
1. Hike the trails of the Pawling Nature Reserve
The Pawling Nature Reserve is a beautiful destination for outdoor enthusiasts. It features various trails that wind through forests, fields, and wetlands. The scenery is breathtaking, offering views of diverse ecosystems and wildlife.
You can choose from different trails based on your fitness level and preference. Each trail provides an opportunity to connect with nature closely. Whether you are hiking solo or with family, everyone can find enjoyment here.
The reserve is home to many species of birds and small animals. So, don’t forget your binoculars if you enjoy birdwatching! It’s a perfect spot to take photos and make lasting memories.
The best time to visit is during the fall when the leaves change colors. The vibrant hues create a picturesque backdrop that enhances the experience of hiking. Summer days also offer a refreshing escape into nature.
Be sure to carry water and snacks for your hike. Remember to respect the natural environment by staying on marked paths. Pawling Nature Reserve is waiting for you to explore its beauty!
Address: 102 Eastdell Rd, Pawling, NY 12564.
2. Explore the Appalachian Trail
The Appalachian Trail is a renowned hiking route that stretches over 2,190 miles, traversing 14 states. In Pawling, you have access to this iconic trail. It guides you through stunning landscapes, including mountains, valleys, and forests.
You can enjoy various sections of the trail. Some parts are more challenging and perfect for seasoned hikers. Other areas are suitable for families and beginners. Each section offers an adventure through nature’s beauty.
The trail is well-marked and maintained, making navigation straightforward. As you walk, you can discover unique flora and fauna along the way. Observing the changing scenery is part of the joy of hiking.
Many hikers take short trips or day hikes. The fresh air and exercise can invigorate your spirit. Plus, it’s a great way to unplug and connect with nature.
Remember to pack accordingly, including plenty of water and snacks. Whether you hike a mile or several, the Appalachian Trail is a must-visit for nature lovers in Pawling!
Address: Appalachian Trail Parking, Pawling, NY 12564.
3. Enjoy a day of fishing or picnicking at Whaley Lake
Whaley Lake is a serene spot for fishing and picnicking. The calm waters provide an excellent environment to relax and enjoy nature. You can catch various fish here, making it perfect for fishing enthusiasts.
Pack a picnic basket, and enjoy a meal while taking in the beautiful surroundings. There are picnic tables available near the water, providing a perfect spot to unwind. The sound of nature enhances the peaceful atmosphere.
If you’re not into fishing, you can also take a leisurely stroll along the shore. People often enjoy watching the sunset over the lake. It creates stunning views that are perfect for photography.
Bring your family and friends for a day of fun. Whaley Lake is often less crowded than other local spots, allowing for a genuine experience with nature. It’s a great way to escape the daily grind and recharge.
Don’t forget your sunscreen and hat! Enjoy a peaceful day at Whaley Lake; it might just become your favorite getaway.
Address: Whaley Lake, Pawling, NY 12564.
4. Visit the historic John Kane House
The John Kane House is a historical gem in Pawling. This beautiful structure showcases the rich history of the area. Built in the 19th century, it offers a glimpse into Pawling’s past.
When you visit, you can explore the architecture and learn about its significance. The house has been well-preserved, maintaining its original charm. It often hosts events and educational programs as well.
The House is an ideal spot for history buffs, families, and curious visitors. You’ll find knowledgeable guides who can share fascinating stories about the house and its former residents. Each corner of the house has a story to tell!
Take time to roam the surrounding grounds and appreciate the beautiful landscapes. The historical aspect paired with stunning scenery makes it a worthwhile visit.
Make sure to check the visiting hours before you go. The John Kane House is a wonderful way to soak in some local history and connect with the past.
Address: 84-90 East Main St, Pawling, NY 12564.
5. Catch a live performance and enjoy dining at Daryl’s House
Daryl’s House is a popular music venue and restaurant located in Pawling. It is known for hosting live performances from various artists. The atmosphere is vibrant, creating an enjoyable experience for music lovers.
The venue offers an extensive menu, allowing you to indulge in delicious food while enjoying fantastic music. Whether you prefer appetizers or entrees, there’s something for everyone. The combination of great food and live music makes every visit special.
Daryl’s House frequently features both upcoming and established musicians. It’s a great chance to see live shows in an intimate setting. The energy of a live performance adds to the dining experience.
Make sure to check the event schedule to find an act that interests you. It’s a perfect spot for a night out with friends or a romantic dinner.
Don’t forget to make reservations, especially on weekends. Experience the magic of live music and delightful dining at Daryl’s House! You are sure to have a memorable evening.
Address: 130 NY-22, Pawling, NY 12564.
6. Savor baked goods and artisanal bread at the Pawling Bread Co.
Pawling Bread Co. is a local bakery that captures the heart with its delicious offerings. You can find a wide selection of artisanal bread and baked goods. Each item is crafted with care and attention to detail.
Whether you prefer a sweet pastry or a hearty loaf of bread, you won’t be disappointed. The aroma of fresh bread baking fills the air, enticing you to try something new. Each bite reveals the quality and flavor of the ingredients.
The bakery focuses on using high-quality, local ingredients, ensuring fresh flavors. You can also find gluten-free options, making it inclusive for everyone. It’s a perfect spot to grab a treat for breakfast or an afternoon snack.
Don’t forget to try their seasonal specialties! They often feature items that reflect local flavors and holidays, adding variety to your experience.
The warm and welcoming environment invites you to sit and enjoy your baked goods on-site. Visit Pawling Bread Co. to indulge your senses and enjoy the taste of homemade goodness.
Address: 2 E Main St, Pawling, NY 12564.
7. Indulge in delicious BBQ at Big W’s Roadside Bar-B-Que
Big W’s Roadside Bar-B-Que is the go-to spot for BBQ lovers in Pawling. This casual eatery serves mouth-watering barbecue dishes that are full of flavor. The aroma alone will make your mouth water!
You can choose from various meats, including ribs, pulled pork, and brisket. Each dish is cooked to perfection, ensuring a delightful culinary experience. The menu also includes delicious sides, like coleslaw and cornbread.
Big W’s emphasizes quality and flavor, making it a favorite among locals and visitors alike. Many people love to grab takeout and enjoy it outdoors at nearby parks.
The relaxed atmosphere and friendly service make it a great place to unwind. It’s perfect for family dinners or casual outings with friends. Everyone leaves with full bellies and smiles!
Make sure to stop by Big W’s after a day of exploring Pawling. Savor the delicious BBQ that awaits you—you won’t be disappointed!
Address: 29 E Main St, Pawling, NY 12564.
8. Relax at Lake Peekskill
Lake Peekskill is a charming spot for relaxation and outdoor fun. This family-friendly destination is a short drive from Pawling. Whether you enjoy swimming, fishing, or picnicking, there are activities for everyone.
The lake is surrounded by beautiful scenery, providing a tranquil escape from everyday life. You can spend the day in the sun, enjoying the soft breeze and scenic views. Bring your beach towel and enjoy a peaceful day by the water.
Families can take advantage of the picnic areas, where you can share meals and laughter together. There are playgrounds nearby for children, ensuring that everyone has fun.
The lake also offers boating and kayaking options, allowing your family to explore the water. Rentals are available if you don’t have your own equipment.
Visiting Lake Peekskill is a perfect way to enjoy outdoor activities while making wonderful memories. Unwind by the water and appreciate the beauty of nature in this relaxing setting.
Address: 113 Lake Dr, Peekskill, NY 10566.
9. Play a round of golf at the Pawling Country Club
Pawling Country Club offers a fantastic golfing experience for players of all skill levels. The beautifully landscaped course provides a serene setting for a day on the greens. Each hole offers unique challenges, making it an exciting game.
Whether you are a beginner or an experienced golfer, the club welcomes everyone. Take a lesson from a professional to improve your skills or enjoy a casual round with friends. The club also hosts tournaments throughout the year for those looking for friendly competition.
After a round of golf, you can relax in the clubhouse, which offers great amenities. Enjoy a meal or a drink while reflecting on your game. The atmosphere is friendly and inviting, adding to the overall experience.
Pawling Country Club’s picturesque views enhance your time spent on the course. The natural beauty surrounding the course adds to the enjoyment of your game.
Plan your visit to Pawling Country Club for a day of golfing fun and relaxation. It promises a fulfilling experience for all golf enthusiasts!
Address: 20 Aster Rd, Pawling, NY 12564.
10. Attend a local event or workshop at the Pawling Library
The Pawling Library is not just about books; it’s a vibrant community hub. You can find a variety of local events and workshops happening throughout the year. From art classes to book clubs, there’s something for everyone!
Attending an event at the library is a great way to meet new people and connect with the community. You can learn new skills or dive into exciting topics through workshops and lectures. The library’s inviting atmosphere makes it easy to engage with others.
Many programs are tailored for kids as well, fostering a love for reading. Story time and craft events for children will spark their imagination and creativity.
The library also hosts seasonal events, like summer reading programs and holiday celebrations. These events often incorporate local culture and traditions, making them even more special.
Visiting the Pawling Library makes learning fun and engaging. Participate in the community and discover something new next time you stop by!
Address: 11 Broad St, Pawling, NY 12564.
11. Discover the beauty of Canopus Lake in nearby Fahnestock State Park
Canopus Lake is a stunning natural haven located in Fahnestock State Park. This charming lake is perfect for a day of exploration and outdoor fun. Whether you enjoy hiking, fishing, or simply soaking in the scenery, it’s a great choice for all ages.
The surrounding park offers miles of beautiful trails varying in difficulty. You can explore them on foot or on a bike. The refreshing beauty of nature is uplifting, making each hike unique and enjoyable.
Fishing at Canopus Lake is a favorite pastime. Cast your line and see what you can catch while relaxing by the water. It’s also a great spot for picnicking, with scenic views creating the perfect backdrop for a meal.
The park is rich in wildlife, so keep an eye out for local birds and animals. There are plenty of places to sit and simply watch nature unfold around you.
Visit Canopus Lake for a delightful day of outdoor activity and calm. It’s a perfect getaway to experience the beauty of the Hudson Valley!
Address: 1519 NY-301, Carmel, NY 10512.
12. Take a scenic drive through picturesque Dutchess County
Driving through Dutchess County is a delightful way to experience the region’s charm. The scenic routes lead you through rolling hills, beautiful farms, and quaint towns. Each twist and turn showcases breathtaking views of the landscape.
Don’t rush; take your time to enjoy the sights along the way. There are numerous overlooks where you can pull over and appreciate the scenery. Autumn is especially beautiful when the leaves turn to warm hues.
As you navigate the roads, stop by local shops and farmers markets. Supporting local businesses is rewarding and allows you to discover unique items. You might find handmade crafts or fresh produce to enjoy.
Plan a day to explore and take in the beauty of the area. Bring your camera to capture the picturesque moments you encounter.
Dutchess County is not just about the destination; it’s about the journey. Enjoy every moment spent on these scenic drives—it’s a hidden gem waiting for you!
Address: Dutchess County, NY.
13. Enjoy a meal with a view at The Old Thyme Restaurant
The Old Thyme Restaurant is the perfect blend of delicious food and stunning views. Nestled in Pawling, this eatery offers a variety of dishes that cater to all tastes. From comfort food to gourmet options, there is something to satisfy everyone.
As you dine, take in the beautiful scenery from the restaurant’s windows. The charm of the surroundings enhances the experience, making it a lovely place for family dinners or special occasions.
The restaurant prioritizes using fresh, locally sourced ingredients. This ensures that every dish packs a punch of flavor. Their seasonal specials are a must-try, reflecting the bounty of the region.
Whether you choose a hearty breakfast, lunch, or dinner, you’ll leave feeling satisfied and happy. The friendly staff adds to the welcoming atmosphere, making you feel right at home.
Make a reservation to enjoy a meal at The Old Thyme Restaurant. It’s a delightful spot to relish great food while appreciating the view!
Address: 23 W Main St, Pawling, NY 12564.
14. Browse local art and crafts at the Pawling Farmers Market
The Pawling Farmers Market is a fantastic place to discover local art and crafts. Open on weekends, it showcases the work of local artisans and farmers. You’ll find everything from handmade goods to fresh fruits and vegetables.
Strolling through the market is enjoyable and supports the community. You can interact with vendors, learning about their crafts and passion for their products. It’s a great way to connect with local talent and discover unique gifts.
Art enthusiasts will appreciate the variety of handmade crafts available for purchase. From pottery to paintings, you’ll find items that reflect the local culture and creativity. It’s perfect for finding something special to bring home!
The market is often lively with music and local performances, creating a vibrant atmosphere. Grab a bite to eat from one of the food stalls and sit back to enjoy the ambiance.
Visiting the Pawling Farmers Market is more than shopping; it’s about experiencing the heart of the community. Don’t miss it during your visit to Pawling!
Address: 4402 NY-22, Pawling, NY 12564.
15. Unwind with nature at Great Swamp
Great Swamp is a tranquil natural oasis just waiting to be explored. This beautiful wetland offers easy hiking trails, making it accessible for all ages. You can stroll the paths and immerse yourself in the sights and sounds of nature.
Birdwatchers will love the diverse bird species that inhabit the area. Bring your binoculars, and you might spot some fascinating wildlife! You can also enjoy a peaceful afternoon fishing or simply relaxing by the water.
There are plenty of picnic spots to take a break and enjoy your packed lunch. The serene environment encourages visitors to pause and appreciate their surroundings. It’s not unusual to see families enjoying the outdoors together here.
Great Swamp provides a variety of educational programs throughout the year. These programs often focus on the local ecosystem and wildlife. It’s a perfect opportunity to learn more about nature.
Make Great Swamp a stop during your visits to Pawling; it’s a perfect spot to unwind and rejuvenate surrounded by nature!
Address: 421 W Main St, Pawling, NY 12564.
16. Visit Seward Park
Seward Park is a perfect community park ideal for family outings and leisurely strolls. Located in Pawling, the park features expansive green spaces and picnic areas. It’s a great place to spend a sunny afternoon outdoors.
You can play on the playground or kick a soccer ball on the open fields. The park offers plenty of activities for children, making it a family-friendly destination. Bring a ball or Frisbee for added fun!
Walking paths wind through the park, ideal for leisurely strolls or morning jogs. As you walk, enjoy the natural beauty around you. The inviting atmosphere is perfect for unwinding with family or friends.
Pawling residents often gather at Seward Park for community events and activities. Check the local calendar for any fun happenings during your visit.
Take time to relax at Seward Park—enjoy nature, play games, or simply bask in the sunshine. It’s a wonderful place to create lasting memories!
Address: 20 Seward Ave, Pawling, NY 12564.
17. Explore the historic buildings at the Pawling Historic District
The Pawling Historic District is a well-preserved area filled with charming old buildings. Walking through this district transports you back in time. Each structure has its own story, reflecting the rich history of Pawling.
As you stroll along the streets, take note of the beautiful architecture. Many buildings have unique styles and details that are worth appreciating. You can visit homes and businesses that date back to the 18th century!
The Historic Society often offers guided tours, providing insight into the people and events that shaped Pawling. Engaging with the local history will add depth to your visit. Listen to tales that offer a glimpse into the past.
Don’t forget to take plenty of photos. The picturesque streets are perfect for capturing beautiful memories. Some locations also have plaques detailing their history, allowing for self-guided exploration.
Discover Pawling’s heritage by visiting the Historic District. It’s an enriching experience that highlights the community’s past and charm!
Address: Pawling Historic District, Pawling, NY 12564.
18. Participate in seasonal activities at nearby Pawling’s Lavender Farm
Pawling’s Lavender Farm is a delightful spot to visit, especially in the summer when the lavender is in bloom. Participate in seasonal activities that celebrate this beautiful plant. The farm is known for its breathtaking fields of lavender that attract visitors from afar.
You can take guided tours to learn about the growing process and the different lavender varieties. The fresh scent fills the air, creating a relaxing atmosphere. During harvest season, you can also pick your own lavender—an enjoyable and rewarding experience!
Workshops are offered seasonally, where you can craft items like essential oils, soaps, and sachets. It’s a unique opportunity to create something special to take home. Seasonal events also include festivals and markets celebrating the beauty of lavender.
The friendly farm staff makes every visitor feel welcome and encourages exploration. You can also find lavender-related products available for sale in their shop.
Visit Pawling’s Lavender Farm to enjoy nature, creativity, and community. It’s a memorable experience that delights the senses!
Address: 2047 NY-55, Pawling, NY 12564.
19. Enjoy berry-picking at Blooming Hill Farm
Blooming Hill Farm is a delightful destination for berry picking. Located a short drive from Pawling, this family-run farm offers a fun outdoor experience for everyone. Depending on the season, you can pick strawberries, blueberries, and more!
Berry-picking is a fun activity that allows you to connect with nature. The farm provides baskets to collect your freshly picked berries. You can harvest them at your own pace while enjoying the sunny outdoors.
Blooming Hill Farm also emphasizes sustainable farming practices, ensuring the best quality produce. Besides berries, you can find various seasonal vegetables and flowers available for sale.
This is a wonderful way to teach children about where their food comes from. The farm is vibrant with friendly staff who love to share their knowledge about farming and harvesting.
Visiting Blooming Hill Farm for berry-picking is a delightful way to spend a day outdoors. Create sweet memories as you fill your basket with fresh fruit!
Address: 70 Blooming Hill Rd, Montgomery, NY 12549.
20. Experience live theater performances at the Pawling Theatre Company
The Pawling Theatre Company is a hidden gem for theater enthusiasts. This local theater produces a variety of performances throughout the year. From classic plays to contemporary shows, there’s always something entertaining on stage.
Attending a live performance creates a fun and engaging experience. The talented actors bring stories to life right before your eyes. Each show offers its unique charm, captivating audiences with powerful performances.
The intimate setting allows for a closer connection to the performers and the story. It’s a perfect destination for a date night, a family outing, or a gathering with friends.
Check the theater schedule to find a show that interests you. Special events and community productions are also common and worth attending.
Support local arts by visiting the Pawling Theatre Company. It’s a fantastic way to enjoy culture and entertainment in the heart of Pawling!
Address: 17 East Main St, Pawling, NY 12564.
21. Take a guided kayak tour on the Housatonic River nearby
Exploring the Housatonic River by kayak is an exciting adventure. The river, nearby Pawling, offers guided tours perfect for adventurers of all skill levels. Paddle along the beautiful waterways as you soak in the stunning scenery and wildlife.
Guides lead you through the best spots, sharing information about the river’s ecosystem. You’ll get to see a variety of birds, fish, and plant life along the banks. The peaceful environment is a great way to unwind and connect with nature.
Most tours provide all necessary gear, including kayaks and life jackets. Just bring your enthusiasm and a camera to capture the memories! Kayaking is a splendid way to explore the scenic beauty of the Housatonic River.
Whether you’re looking for a relaxing day on the water or some invigorating exercise, kayaking is a fabulous option. Many tours run during the summer months, so plan accordingly!
Experience the thrill of a guided kayak tour on the Housatonic River. It’s an adventure you won’t want to miss!
Address: Housatonic River, Lee, MA 01238.
22. Visit nearby Storm King Art Center
The Storm King Art Center is a remarkable destination for art lovers. Located just a short drive from Pawling, this open-air museum features large-scale sculptures set against stunning landscapes. The beautiful grounds create a unique experience in the world of contemporary art.
As you stroll through the grounds, you’ll discover various artworks from renowned artists. The combination of art and nature is breathtaking, providing a visual feast for visitors. You can also participate in guided tours to gain insight into the artworks and artists.
The center encourages interaction with the art, allowing you to immerse yourself in creativity. The tranquil atmosphere adds to the overall experience, making it enjoyable for both individuals and families.
Plan your visit during the warmer months to take full advantage of the expansive outdoor space. Many people bring picnic blankets to enjoy a meal amidst the art.
A visit to Storm King Art Center offers a perfect blend of culture and nature. It’s a must-see while in the Pawling area for an inspiring day!
Address: 1 Museum Road, New Windsor, NY 12553.
23. Relax at Mason Park
Mason Park is a peaceful retreat in Pawling, perfect for relaxation and leisure. The park features serene walking trails and well-maintained green spaces for picnics. It’s a great spot to unwind and enjoy the beauty of nature.
Visitors can stroll through the trails, taking in sights of local flora and fauna. The tranquil atmosphere encourages quiet reflection, making it an ideal spot to read a book or enjoy some quiet time.
Families often visit Mason Park for picnics, appreciating the shade from trees and the open spaces for children to play. There’s plenty of room to run around or engage in outdoor games.
In the summer, the park often hosts local events, adding vibrancy to the area. You might catch live music or community gatherings that bring people together.
Plan a visit to Mason Park for a soothing escape from the hustle and bustle. It’s an excellent choice for anyone seeking a peaceful day outdoors!
Address: 1 Pawling Ave, Pawling, NY 12564.
24. Explore the scenic beauty of Hudson Highlands State Park
Hudson Highlands State Park is a stunning natural area with breathtaking views and diverse trails. The park covers a vast area, featuring mountains and ridges with scenic vistas that are awe-inspiring. It’s a perfect destination for hiking, biking, or simply enjoying the outdoors.
The well-marked trails offer various levels of difficulty, catering to everyone from beginners to experienced hikers. Hiking through the park allows you to connect with nature while experiencing the area’s beauty up close.
As you explore, you’ll find incredible views of the Hudson River and surrounding landscapes. The park is teeming with wildlife, and you may spot various birds, deer, and other animals.
Many visitors enjoy picnicking at designated areas, making for perfect weekend getaways. You can also find opportunities for rock climbing for those seeking a more adventurous experience.
Visit Hudson Highlands State Park for a day of adventure, exploration, and unforgettable views. The beauty of the park awaits you!
Address: 3161 NY-9D, Cold Spring, NY 10516.
25. Discover the Dutchess County Rail Trail
The Dutchess County Rail Trail is perfect for walking, running, or biking. This beautifully maintained trail spans over 13 miles, providing an excellent way to explore the stunning scenery of Dutchess County. You’ll find scenic views, old railroad trestles, and bridges along the route.
The paved trail is accessible for all skill levels and is often used for leisurely strolls or family outings. Many sections are shaded by trees, providing a comfortable experience while enjoying the fresh air.
There are several access points along the trail, making it easy to plan shorter or longer trips. Along the way, you will find picnic areas and parks, creating perfect spots to rest and appreciate the surroundings.
It’s common to see families, joggers, and cyclists enjoying their time on the trail. The Rail Trail promotes an active lifestyle while encouraging connections with nature.
Spend a day exploring the Dutchess County Rail Trail—it’s a fantastic way to experience the natural beauty of the region while enjoying outdoor activities!
Address: The Rail Trail connects various locations throughout Dutchess County, NY.
Final Thoughts
Pawling, NY, offers a wonderful array of activities for visitors, from scenic outdoor adventures to cultural experiences. Each destination embodies the beauty and charm of this unique area. Whether you’re hiking through lush trails, exploring historic sites, or enjoying local cuisine, there’s something for everyone to enjoy.
Your exploration of Pawling creates lasting memories of tranquility and adventure. It’s a community that welcomes you with open arms, inviting you to explore its hidden gems. Immerse yourself in nature, engage with local culture, and discover the joys this beautiful town has to offer!
For more exciting destinations in New York, check out our guide on places to visit in New York. You can also explore best weekend getaways in New England for more travel inspiration!