Old Saybrook, Connecticut Travel Guide – History, Travel, Hotels, and More!

Old Saybrook, a charming coastal town in Connecticut, offers a perfect blend of New England charm and modern amenities. This historic gem, founded in 1635, boasts unique shops, diverse dining, and scenic beaches that make it an ideal destination for travelers seeking a quintessential New England experience.

You’ll find plenty to do in Old Saybrook. The town’s beautiful shoreline along Long Island Sound provides opportunities for relaxation and water activities. Stroll through the quaint downtown area, where you can explore local boutiques and savor fresh seafood at waterfront restaurants.

History buffs will enjoy the Old Saybrook Historical Society’s walking tour, which showcases the town’s rich past. Nature lovers can explore lush coastal forests and enjoy bird watching.

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Whether you’re looking for a peaceful getaway or an active vacation, Old Saybrook’s small-town atmosphere and scenic beauty make it a must-visit destination in Connecticut.

How to Get to Old Saybrook

Getting to Old Saybrook is easy with several transportation options available. By train, you can take Amtrak from major cities like Boston or New York. The Amtrak Northeast Regional line stops directly in Old Saybrook. For a more local option, Shore Line East commuter rail connects Old Saybrook to New Haven and other Connecticut towns.

Driving is convenient if you’re coming from nearby. Old Saybrook is located just off I-95, making it easily accessible by car.

If you’re flying in, the closest major airports are:

Bradley International Airport (Hartford) – about 1 hour drive
T.F. Green Airport (Providence) – about 1.5 hour drive
Logan International Airport (Boston) – about 2.5 hour drive

Once in Old Saybrook, you can explore the charming town on foot or rent a bike to cruise along the scenic coastline. Remember to check schedules and book tickets in advance, especially during peak travel seasons. With these options, your journey to Old Saybrook will be smooth and stress-free.

What to See in Old Saybrook

Old Saybrook offers a mix of natural beauty and cultural attractions. You can start your visit at Fort Saybrook Monument Park, which overlooks the Connecticut River. It’s a great spot to learn about local history and enjoy scenic views. For beach lovers, Harvey’s Beach is a must-visit. This sandy stretch is perfect for swimming and sunbathing. You can also explore the coastal forest at nearby Rocky Neck State Park.

Main Street is lined with unique shops and boutiques. It’s an ideal place for shopping and grabbing a bite to eat – very similar to Sausalito, California. Don’t miss the chance to try a delicious lobster roll at one of the local seafood restaurants. Art enthusiasts will appreciate the Katharine Hepburn Cultural Arts Center. This venue hosts various performances and exhibitions throughout the year.

For a taste of luxury, you can visit Saybrook Point Resort. Even if you’re not staying there, the marina offers beautiful views of Long Island Sound. Nature lovers should keep an eye out for eagles and ospreys, often spotted near the river. The area’s natural beauty makes it a perfect spot for sailing or simply enjoying the coastal scenery.

Read our articles on the best things to do in Old Saybrook, Connecticut and best restaurants in Old Saybrook, Connecticut for even more ideas!

Where to Stay in Old Saybrook

Read our article on hotels near Old Saybrook, Connecticut for the best options for your stay. Here’s a short list of some options:

If you’re looking to stay in a vacation home, apartment, BnB, or VRBO in Old Saybrook, Connecticut, we recommend you search on VRBO, Hotels.com, and Booking.com for up-to-date options.

History of Old Saybrook

Old Saybrook, Connecticut, boasts a rich history dating back to 1635. It began as Saybrook Colony, one of the earliest English settlements in North America. The town’s past is filled with notable figures and landmarks. You’ll find the General William Hart House, a beautifully preserved 18th-century home, offering a glimpse into colonial life.

Old Saybrook’s Historical Society maintains several historic sites. They provide guided tours and exhibitions that bring the town’s past to life. Famous residents have left their mark on Old Saybrook. The legendary actress Katharine Hepburn called this charming coastal town her home for many years. As you stroll through the town, you’ll notice well-preserved architecture from various periods. The historic district features buildings dating back to the 17th century.

Old Saybrook’s history is closely tied to its maritime heritage. The town’s location at the mouth of the Connecticut River made it a strategic port in early American history. Today, Old Saybrook seamlessly blends its historic charm with modern amenities.

Towns Near Old Saybrook

Old Saybrook’s charm extends to its neighboring towns, offering you a diverse range of experiences. Just a short drive away, you’ll find Essex, a picturesque village known for its stunning waterfront and historic architecture.

Essex boasts a quaint Main Street lined with boutique shops and cozy restaurants. You can take a ride on the Essex Steam Train for a nostalgic journey through the Connecticut River Valley.

Old Lyme, located across the Connecticut River, is a haven for art lovers. The town is home to the Florence Griswold Museum, showcasing American Impressionist paintings.

Both Essex and Old Lyme offer beautiful beaches and parks for outdoor enthusiasts. You can enjoy kayaking, fishing, or simply relaxing by the water.

These nearby towns complement Old Saybrook perfectly, giving you a well-rounded Connecticut experience. Each has its own unique attractions and charm, making them worth exploring during your visit.

Old Saybrook 2025 Deals!
Get a discount of 15% to 70% on accommodation in Old Saybrook! Look for deals here:
Old Saybrook Hotels, Apartments, B&Bs