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Points of Interest between Bristol, Rhode Island to Oyster Bay, New York

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picture of Bristol, Rhode Island

Five Unexpected Places to Stop on a Drive from Bristol, Rhode Island and Oyster Bay, New York

If you're looking for a scenic drive with plenty of unexpected stops along the way, look no further than a road trip from Bristol, Rhode Island, to Oyster Bay, New York. This route takes you through stunning coastal towns, historic landmarks, and unexpected treasures. The trip can be completed in about four hours without stops, but we recommend taking your time to enjoy the sights.

The halfway point of this trip is Guilford, CT, a charming town with a rich history and plenty of things to do. Make sure to stop here for a break and explore the area. Take a stroll down the main street lined with boutique shops and quaint restaurants, or check out some of the local museums and galleries. There's something for everyone in Guilford.

1. Watch Hill, Rhode Island

Watch Hill is a seaside village in Westerly, Rhode Island, that's a must-see spot on this road trip. The town has a charming New England feel, with colorful cottages and quaint shops. Take a walk along the beach to watch the sunset, or visit the iconic Ocean House, a grand hotel built in 1868 that has recently been restored to its former glory. Don't miss out on the fresh seafood at the Olympia Tea Room, a local favorite.

2. Block Island, Rhode Island

Block Island is a small island off the coast of Rhode Island that's known for its beaches and nature preserves. The island is a popular destination for summer tourists, but it's worth a visit any time of year. The Mohegan Bluffs are a must-see, with stunning views of the ocean and sweeping cliffs. Stop at The Oar, a local restaurant known for its famous Bloody Marys and lobster rolls.

3. Mystic, Connecticut

Mystic, Connecticut, is a historic town that's home to the Mystic Seaport Museum, a living history museum that brings the maritime history of the region to life. Take a walk through the town's historic district to see the restored homes and buildings from the 18th and 19th centuries, or take a ride on the Mystic Riverboat for a unique view of the town. Don't miss the pizza at Mystic Pizza, made famous by the 1988 movie of the same name.

4. Guilford, Connecticut

As the halfway point of the road trip, Guilford is a perfect spot to stop for a break and discover this charming town. The Henry Whitfield State Museum is the oldest house in Connecticut and a must-see for history buffs. The town green hosts events and farmers markets, and there are plenty of shops and restaurants to explore. Make sure to stop at The Place, a seasonal restaurant known for its outdoor seating and delicious seafood.

5. Port Jefferson, New York

Port Jefferson is a historic village on Long Island's North Shore that's known for its maritime history and beautiful architecture. The village has a wide selection of shops and restaurants, including Danfords Hotel & Marina, a waterfront hotel that's perfect for a luxurious overnight stay. Don't miss out on a visit to the Port Jeff Brewing Company for delicious craft beer and pub food.

If you're looking for a unique road trip filled with unexpected surprises, this route from Bristol to Oyster Bay will not disappoint. From charming coastal towns to historic landmarks, there's something for everyone along the way. So pack your bags, hop in the car, and embark on an adventure you won't soon forget.

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