Oyster Bay is a charming coastal town filled with fun things to do and see. With its beautiful beaches, lush parks, and rich history, there’s something for everyone. Whether you’re looking for family-friendly activities, outdoor adventures, or a peaceful place to relax, Oyster Bay has it all. You can stroll along the waterfront, visit interesting museums, or enjoy delicious local dining options.
In this guide, we will be sharing some of the top activities and attractions in Oyster Bay. You’ll find great spots for picnics, unique shops to browse, and exciting events throughout the year. Get ready to discover the magic of this lovely town!
Things to Do in Oyster Bay
1. Visit Planting Fields Arboretum State Historic Park
Planting Fields Arboretum State Historic Park is a hidden gem in Oyster Bay. This vast estate features over 400 acres of beautiful gardens, walking paths, and greenhouses. You can wander through a diverse collection of plants, including rare trees and vibrant flowers.
The park is perfect for a leisurely stroll or a family picnic. Don’t miss the stunning Camellia Greenhouse, which houses exotic plants and seasonal displays. It’s a favorite spot for photography enthusiasts as well. Throughout the year, the arboretum hosts special events and educational programs for all ages.
Children can enjoy nature scavenger hunts while adults can join guided tours to learn about the estate’s history. The park is also home to charming little trails where you might spot local wildlife. Each season brings a unique charm. In autumn, the foliage turns to vibrant shades of orange and red.
Whether you’re a plant lover or just looking for a peaceful escape, Planting Fields will not disappoint. Visitors often leave feeling rejuvenated and inspired by the natural beauty surrounding them.
Address: 1395 Planting Fields Rd, Oyster Bay, NY 11771.
2. Tour Sagamore Hill National Historic Site
Sagamore Hill National Historic Site was once the summer home of Theodore Roosevelt, the 26th President of the United States. Located in Oyster Bay, this grand estate offers a glimpse into the life of one of America’s most beloved leaders. The house, built in the late 1800s, showcases Roosevelt’s eclectic style and fascinating personal artifacts.
You can take guided tours that explore both the house and the surrounding gardens. The knowledgeable rangers share stories about Roosevelt’s life, character, and political achievements. Don’t forget to check out his impressive collection of books and trophies, which reflect his adventurous spirit.
The grounds are equally captivating, with pleasant walking trails through lush greenery. It’s an ideal place for a family outing. Visitors often enjoy picnicking near the beautiful views of Oyster Bay that the estate provides.
With educational programs and special events, Sagamore Hill is a hub for history enthusiasts. The site also emphasizes conservation and Roosevelt’s dedication to preserving the American environment.
Address: 20 Sagamore Hill Rd, Oyster Bay, NY 11771.
3. Stroll through Theodore Roosevelt Memorial Park
Theodore Roosevelt Memorial Park is a beautiful spot for relaxation and recreation in Oyster Bay. Located right on the waterfront, this park offers stunning views of the bay and surrounding area. You can stroll along the walking paths while enjoying the fresh sea air.
The park is well-equipped with playgrounds, making it perfect for families. Children can play while parents relax on benches or at picnic tables. From here, you can also access the beaches, where you can take a dip or just enjoy the sands.
Throughout the year, various community events take place here, bringing people together for fun activities. Whether it’s a concert, movie night, or local festival, there’s always something happening. The park also has lovely green spaces for those who appreciate nature.
During the warmer months, the area becomes vibrant with flowers and wildlife. Fall offers a stunning backdrop with colorful leaves, making it a picturesque place for a visit any time of the year.
Address: 49 W Shore Rd, Oyster Bay, NY 11771.
4. Check out Raynham Hall Museum
Raynham Hall Museum is a must-visit for history lovers. This beautifully preserved 18th-century home was once the residence of the prominent Townsend family. Today, it serves as a museum highlighting the local history of Oyster Bay and the revolutionary era.
During your visit, you can explore various exhibits featuring artifacts and artwork from the time period. The knowledgeable volunteers provide guided tours filled with interesting stories about the house and its inhabitants. The tours give you a real feel for life in the 1700s.
The gardens surrounding the museum are also worth exploring. They provide a lovely backdrop for a peaceful stroll. The museum frequently hosts events, including lectures and workshops, making it a lively hub for education and engagement.
Artifacts within the museum tell the story of Oyster Bay’s role in the American Revolution. Often, there are special exhibitions focusing on different aspects of history, making each visit unique.
Address: 20 Raynham Rd, Oyster Bay, NY 11771.
5. Shop at 20th Century Cycles
20th Century Cycles is a unique bicycle shop that pays homage to cycling culture and history. Located in Oyster Bay, it’s not just a business but a local landmark connected to Billy Joel, who has often visited it. As you walk in, you’ll notice walls adorned with vintage bicycles and memorabilia.
The store offers a wide range of bicycles for sale, from modern designs to classic models. You can find everything you need for cycling, whether you’re a seasoned pro or just getting started. The staff is friendly and knowledgeable, always ready to assist you in finding the right bike and gear.
Besides bikes, they also host events and workshops. These gatherings are fun and engage the biking community, making it a great place to meet fellow cycling enthusiasts. After shopping, consider taking a short ride along the nearby trails to test your new purchase.
Visiting 20th Century Cycles is an experience, combining shopping with a bit of local history. Don’t miss the chance to stop by during your Oyster Bay adventure!
Address: 16 W Main St, Oyster Bay, NY 11771.
6. Explore the Oyster Bay Railroad Museum
The Oyster Bay Railroad Museum is a delightful destination for both history buffs and families. Housed in a historic railroad station, the museum celebrates the significant role that railroads have played in the development of the Oyster Bay area. You can explore various exhibits showcasing railroad artifacts, photographs, and memorabilia.
One of the highlights includes the chance to board a vintage train car and experience what travel was like decades ago. The museum often hosts special events, such as train rides and community gatherings, making it a lively spot for locals and visitors alike.
The museum is also dedicated to preserving the history of the Long Island Rail Road, with knowledgeable staff ready to share stories and insights. Children especially enjoy the interactive displays and engaging activities that the museum provides.
After exploring the exhibits, consider walking around the surrounding area for more historic sites. The inviting atmosphere and friendly staff make every visit enjoyable and informative.
Address: 102 E Main St, Oyster Bay, NY 11771.
7. Visit the Earle-Wightman House and Garden
The Earle-Wightman House and Garden is a wonderful stop for those interested in local history and architecture. This beautifully restored 19th-century home showcases the lifestyle of early Oyster Bay residents. You can take a guided tour of the house, where you will learn about its architecture and the people who once lived there.
The house is adorned with period furnishings and artifacts that give you a genuine feel of the era. Visitors often comment on how welcoming and informative the tours are. The docents are passionate about the history of the community and are eager to share their knowledge.
The gardens surrounding the house are equally charming, offering a peaceful setting where you can relax and enjoy nature. Seasonal flowers and beautifully landscaped paths make it an inviting place for a leisurely stroll.
Throughout the year, the Earle-Wightman House hosts events, allowing visitors to engage more deeply with history. Special programs for families and children help bring history to life in a fun way.
Address: 140 S. St, Oyster Bay, NY 11771.
8. Hike the trails at Muttontown Preserve
Muttontown Preserve offers nature lovers a fantastic escape from the hustle and bustle. This expansive, preserved area features several scenic trails suitable for all skill levels. You will find various trails leading through beautiful woodlands, meadows, and along peaceful ponds.
As you walk, you may encounter local wildlife, including birds, deer, and other species. The fresh air and tranquil setting make it an ideal location for hiking, running, or simply enjoying nature. Make sure to bring your camera; the landscapes are stunning, especially during autumn.
The preserve also has picnic areas, making it a perfect spot for family outings. After enjoying your hike, you can sit down for a picnic and take in the beautiful surroundings. The trails vary in length, so you can choose an adventure that fits your timeframe.
For those seeking a deeper connection with nature, educational programs are available, offering insights into the local ecosystem and conservation efforts.
Address: 2000 Muttontown Ln, East Hills, NY 11576.
9. Bike along the TOBAY Beach trail
TOBAY Beach offers a lovely bike trail that combines stunning coastal views with a refreshing sea breeze. This scenic route is perfect for cyclists of all ages. As you ride, you’ll enjoy the beautiful sights of the Long Island coastline and the soothing sounds of the waves.
The trail is well-maintained and suitable for leisurely rides and families. Along the way, you will find spots to stop, relax, and take in the landscape. The beach area is welcoming and offers an opportunity to unwind after your ride.
Bring a picnic to enjoy by the shore or stop by a nearby café for a bite to eat. Many families enjoy the playgrounds and picnic areas scattered along the trail. This makes it a great place for social outings and family gatherings.
With a well-marked path and plenty of scenic overlooks, biking along the TOBAY Beach trail is not just exercise; it’s an experience that captures the beauty of Oyster Bay.
Address: 1860 Bay Rd, Massapequa, NY 11758.
10. Kayak the South Shore Blueway Trail
The South Shore Blueway Trail is a thrilling option for adventure seekers and water enthusiasts. Kayaking along this water trail offers a unique way to explore the natural beauty of Oyster Bay and its surrounding areas. You can rent kayaks at several local shops, making it easy to get started.
The trail is suitable for both beginners and experienced kayakers. As you paddle, you’ll have the opportunity to see wildlife up close, including various bird species and maybe even some seals. The calm waters are perfect for a leisure-filled excursion.
Along the way, you can stop at peaceful beaches or picnic spots to take breaks and enjoy the scenery. Many families take advantage of this chance to bond over a fun outdoor activity. Kayaking provides a refreshing way to enjoy the sun and spend quality time together.
Whether you’re exploring alone or with friends, the South Shore Blueway Trail invites you into an enjoyable aquatic adventure. Don’t forget your camera to capture the beautiful moments on the water!
Address: 1860 Bay Rd, Massapequa, NY 11758.
11. Dine at 2 Spring
2 Spring is a must-visit culinary spot in Oyster Bay. This contemporary wine bar offers a relaxed atmosphere and a menu that changes seasonally. Every dish is crafted with fresh ingredients from local farms, showcasing the flavors of the region.
As you settle into a cozy spot, the friendly staff will introduce you to a curated selection of wines perfect for pairing with your meal. Whether you’re in the mood for seafood, meat, or vegetarian options, there’s something for everyone to enjoy.
The ambiance is warm and inviting, making it ideal for casual dining or special occasions. Many visitors rave about the intimate setting, which encourages conversation and a relaxed dining experience. Brunch is also popular here, with a creative menu that includes delicious options.
If you’re looking for something unique, the chefs often create special dishes based on local ingredients. Don’t miss the chance to enjoy a delightful dining experience at 2 Spring!
Address: 2 Spring St, Oyster Bay, NY 11771.
12. Grab a bite at The Homestead
The Homestead is a charming restaurant located in Oyster Bay, known for its relaxed atmosphere and hearty American cuisine. As you enter, you will be greeted by friendly staff and a cozy interior. It’s the perfect spot for a casual meal with family or friends.
The menu offers a variety of delectable options, including burgers, sandwiches, and fresh salads. Each dish is made with quality ingredients and served in generous portions. Many patrons recommend trying the pizza; it’s a local favorite!
The restaurant has a welcoming vibe, making it an ideal place to unwind after a day of exploring the area. You might want to save room for dessert, as they offer delightful treats to satisfy your sweet tooth.
In addition to dining, The Homestead has several events throughout the year. From trivia nights to live music, there’s always something fun happening!
Address: 64 E Main St, Oyster Bay, NY 11771.
13. Indulge in seafood at Wild Honey Restaurant
Wild Honey Restaurant is a delightful seafood spot located right by the water in Oyster Bay. Known for its fresh and flavorful dishes, this restaurant offers a memorable dining experience. The atmosphere is relaxed yet vibrant, making it great for casual dinners or special celebrations.
As you browse the menu, you’ll find various seafood options, from succulent lobster to mouth-watering scallops. They focus on using the freshest local ingredients, ensuring that your meal hits all the right notes. Pair your dish with a selection from their curated wine list for an enjoyable pairing.
Many diners rave about the outdoor seating area. Enjoying your meal while overlooking the bay elevates the dining experience to a whole new level. Don’t forget to save room for dessert; their signature dishes are not to be missed!
Wild Honey is not just about food; it’s about creating a memory. The friendly staff and beautiful ambiance make it a favorite among locals and visitors alike!
Address: 34 W Main St, Oyster Bay, NY 11771.
14. Pick up a quick meal at Harborside Delicatessen
Harborside Delicatessen is the perfect stop for a quick and tasty meal in Oyster Bay. This charming deli offers a variety of sandwiches, salads, and breakfast items. You can grab something to go while you explore the area or enjoy a casual dining experience indoors.
Many locals love the fresh bagels and coffee offered in the morning. It’s a favorite starting point for the day, whether you’re heading to the beach or going for a hike. The deli also has options for those seeking healthier fare, with plenty of fresh salads and vegetarian choices.
In the afternoon, feel free to try one of their famous sandwiches. Their portions are generous, and the flavors are delicious. The ambiance is friendly, and the staff makes everyone feel welcome.
After grabbing your meal, consider taking it to a nearby park or beach for a picnic while enjoying the scenic views. Harborside is all about convenience and comfort in a delightful setting!
Address: 15 W Shore Rd, Oyster Bay, NY 11771.
15. Take a scenic drive along the Oyster Bay waterfront
A scenic drive along the Oyster Bay waterfront is a delightful way to experience the area. The road hugs the coastline, offering breathtaking views of the bay and the charming surroundings. You can take your time and enjoy the sights, making several stops at picturesque spots.
As you drive, keep your eyes peeled for beautiful homes, lush landscapes, and the various boats dotting the water. It’s especially stunning during sunset when the sky lights up with brilliant colors reflecting on the water.
Along the way, you’ll find various parks and beaches, perfect for a quick break or a leisurely stroll. There are also several lookouts where you can snap photos and take in the scenery. This drive is especially enjoyable during the warmer months, when you can feel the refreshing ocean breeze.
For those who appreciate history, an audio guide can enhance the experience by sharing facts about the area. It’s a wonderful way to discover all that Oyster Bay has to offer.
Address: Various viewpoints along Oyster Bay waterfront.
16. Attend events at the Oyster Bay Civic Center
The Oyster Bay Civic Center is a vibrant hub for community events and activities. Located in the heart of the town, it offers a welcoming space for residents and visitors to come together. Throughout the year, various events take place, from art exhibits to live performances.
The center is home to sports facilities, including basketball courts and meeting rooms. It’s a great place for families to engage in recreational activities while meeting other community members. There are regular events designed for all ages, ensuring that there’s something fun happening all the time.
Art lovers will appreciate the art shows and workshops hosted here. It’s an opportunity to explore your creative side or view works from talented local artists.
Additionally, the Civic Center features educational programs that cater to diverse interests. From lectures to classes for adults and kids, everyone can find something to enjoy. Attending an event here promises to be a memorable experience!
Address: 89 W Main St, Oyster Bay, NY 11771.
17. Explore nearby Caumsett State Park
Caumsett State Park is a stunning natural area located just a short drive from Oyster Bay. This expansive park features miles of hiking and biking trails winding through diverse landscapes, including forests and coastal views. It’s a fantastic spot for nature lovers and outdoor enthusiasts.
You can spend hours exploring the park’s beautiful scenery while spotting wildlife along the way. The trails vary in difficulty, making it suitable for families and adventurous hikers alike. Picnic areas are available where you can enjoy a relaxing meal surrounded by nature.
The park is also rich in history, as it was once the estate of Marshall Field, a prominent businessman. Visitors can see the remnants of the estate, which adds a charming historical element to your trip.
In addition to hiking, Caumsett offers opportunities for fishing, birdwatching, and even horseback riding in designated areas. It’s a perfect day trip destination where you can reconnect with nature and enjoy some fresh air.
Address: 25A, Lloyd Harbor, NY 11743.
18. Visit the nearby Cold Spring Harbor Fish Hatchery & Aquarium
The Cold Spring Harbor Fish Hatchery & Aquarium is a fantastic destination for families and nature lovers. Located just a short drive from Oyster Bay, this facility offers visitors a chance to learn about marine life and the importance of conservation. The hatchery breeds and raises various fish species, contributing to the local ecosystem.
Visitors can explore interactive exhibits that provide insights into the aquatic life of the region. The hatchery features tanks with colorful fish, turtles, and even some fascinating reptiles. Children especially enjoy the hands-on activities that let them feel close to wildlife.
Don’t miss the outdoor exhibits, where you can find larger fish species swimming in natural water environments. The serene surroundings of the hatchery are also perfect for a peaceful walk or a picnic.
Throughout the year, the hatchery hosts educational programs and events focused on fish conservation and environment care, making it an excellent option for learning about nature while having fun!
Address: 1660 Route 25A, Cold Spring Harbor, NY 11724.
19. Enjoy a day at Tappen Beach
Tappen Beach is a lovely spot for a day of fun in the sun. Located in Oyster Bay, this beach offers a relaxing atmosphere and scenic views of the water. It’s an excellent destination for families looking to enjoy a day outdoors.
The beach is perfect for sunbathing, swimming, and building sandcastles. The calm waters make it a safe place for children to play. Facilities like restrooms and picnic areas ensure a comfortable beach experience for everyone.
During the summer, you may find activities like beach volleyball and community events happening here. Many families bring snacks or full meals to enjoy on the sand while taking in the lovely surroundings.
As the day winds down, Tappen Beach is also a stunning spot to watch the sunset. The vibrant colors reflecting off the water create a picturesque scene you won’t want to miss. It’s the perfect ending to a wonderful day!
Address: 2 Tappen Beach Rd, Oyster Bay, NY 11771.
20. Check out the local art at the Oyster Bay Historical Society
The Oyster Bay Historical Society is a fantastic destination for art lovers and history enthusiasts alike. The gallery hosts irregular exhibitions and showcases the work of local artists. You can explore various art styles and mediums, making it a beautiful cultural stop in the heart of Oyster Bay.
In addition to the art exhibits, the Historical Society focuses on preserving the rich history of the area. There are often historical displays and artifacts for visitors to explore, shedding light on Oyster Bay’s past. Knowledgeable staff are available to answer questions and provide insights into the exhibits.
The setting itself is charming and welcoming, allowing for an enjoyable browsing experience. Many visitors also appreciate the peaceful atmosphere, making it a perfect spot to spend an hour or two.
Throughout the year, the Society hosts events and workshops that promote local artists and educate the community. Participating in one of these events can enhance your understanding and appreciation of the local art scene.
Address: 20 E Main St, Oyster Bay, NY 11771.
21. Participate in guided tours at the Oyster Bay Historical Society
At the Oyster Bay Historical Society, guided tours provide a fascinating insight into the region’s history. These tours are led by knowledgeable staff who are passionate about sharing their knowledge of the area. You’ll learn about the important events that shaped Oyster Bay and see artifacts that reflect its rich cultural heritage.
The historical buildings on-site add to the experience, offering a glimpse into the architectural styles of different periods. Visitors are often delighted by the personal stories and anecdotes shared during these tours, which bring history to life.
These guided experiences cater to all age groups, making it a wonderful educational opportunity for families. Participants often leave with a deeper appreciation for the town’s past and its future.
Keep an eye on the Society’s calendar for special theme tours and events that happen throughout the year. These unique experiences provide additional layers of engagement with the community.
Address: 20 E Main St, Oyster Bay, NY 11771.
22. Take a tour of the historic houses in Oyster Bay
Oyster Bay is home to several historic houses that offer tours showcasing the rich history of the area. These tours allow visitors to step back in time and explore beautifully preserved homes filled with unique artifacts and intriguing stories. Each house has its unique architectural style and historical significance.
Among the notable houses you can visit are the Raynham Hall and the Earle-Wightman House. Each site offers guided tours that delve into the lives of the families who lived there and their relation to American history. Knowledgeable guides share personal anecdotes that enhance your understanding of the time period.
Many of these historic houses are also surrounded by picturesque gardens, making them a beautiful spot for photography or a quiet moment of reflection. The gardens often feature plants native to the area, complementing the historical significance.
For those passionate about history, participating in these tours provides a deeper connection with the community. Exploring the historic houses will surely enrich your visit to Oyster Bay.
Address: Various historic houses in Oyster Bay.
23. Visit the nearby Long Island Museum of American Art, History, and Carriages
The Long Island Museum of American Art, History, and Carriages is an impressive destination just a short drive from Oyster Bay. This museum features a stunning collection of art dedicated to Long Island’s rich history and culture. You’ll find impressive exhibits ranging from American art to antique carriages.
Each exhibit tells a story of the American experience, showcasing the region’s evolution from its origins to modern times. The museum often hosts special events, workshops, and classes that encourage community engagement and creativity.
One must-see is the carriage collection, which offers a fascinating insight into transportation history on Long Island. Visitors can explore beautifully restored carriages and learn about their importance in everyday life.
The Long Island Museum creates a welcoming environment for all ages. Whether you’re exploring the art galleries or the history exhibits, there truly is something for everyone!
Address: 1200 Route 27A, Stony Brook, NY 11790.
24. Enjoy a sunset at Oyster Bay Town Dock
The Oyster Bay Town Dock is an idyllic spot to unwind and take in stunning sunset views. Located by the water’s edge, it’s a popular gathering place for locals and visitors alike. The scenic setting is perfect for a leisurely stroll along the docks as the sun dips below the horizon.
As the day comes to an end, the surroundings transform into a picturesque landscape filled with vibrant colors reflecting on the water. It’s an opportune moment for photography enthusiasts to capture the beauty of nature.
The Town Dock is also a great spot for picnicking or meeting friends. Many visitors bring chairs or blankets to sit back and relax as they enjoy the enchanting scenery. The peaceful atmosphere enhances the overall experience, allowing you to truly unwind.
With its beautiful sights, Oyster Bay Town Dock is an excellent place to end your day on a perfect note, surrounded by the remarkable beauty of this coastal town.
Address: 1 Bay Ave, Oyster Bay, NY 11771.
25. Explore neighboring Northport village for charming shops and restaurants
Northport Village is a charming destination located just a short drive from Oyster Bay. This quaint village offers an array of delightful shops and eateries, making it a perfect spot for a day of exploration. As you stroll down the picturesque streets, you’ll discover unique boutiques and local businesses.
Whether you’re in the mood for specialty gifts, handmade crafts, or locally-produced goods, Northport has it all. The inviting atmosphere encourages you to take your time as you browse the wares. You’ll likely find friendly shopkeepers happy to share their stories and recommendations.
Don’t miss the dining options available, as Northport offers both casual and fine dining choices. From cozy cafes to upscale restaurants, there’s something to suit every palate. Many establishments focus on fresh, local ingredients, providing a true taste of the region.
Your visit to Northport can be complemented with a stroll along the waterfront, where you can enjoy lovely views of the harbor. It’s a charming destination that adds a delightful touch to your Oyster Bay trip!
Address: Northport, NY 11768.
Final Thoughts
Oyster Bay, New York, is a charming seaside village filled with diverse attractions and activities. Whether you are exploring the stunning natural beauty of its parks or immersing yourself in rich history at historic sites, there’s something for everyone. From delightful restaurants to serene beaches, visitors are sure to create lasting memories.
Each destination, from the spectacular Planting Fields Arboretum to historic Sagamore Hill, offers unique experiences that highlight the culture, history, and beauty of the area. As you explore, the friendly community welcomes you, making your stay enjoyable and fulfilling.
Regardless of your interests, Oyster Bay presents a delightful escape. Whether you’re an outdoor enthusiast, a history buff, or a foodie, you’ll find plenty to engage your senses. For more exploration ideas, check out these best weekend getaways and discover more places to visit like the fascinating places to visit in New York. The beautiful surroundings and vibrant atmosphere draw visitors back time and again, making it a must-visit destination.