- The Wildcat at Lake Compounce: This rollercoaster opened in 1927 and was part of the reason Lake Compounce became one of the best amusement parks in New England. There are also two other rollercoasters and a variety of other rides. Tickets are $30.99 for adults and $28.99 for kids online.
- The Chester-Hadlyme Ferry: The ferry has been transporting people since 1769 – that's more than 240 years. Today, the ferry is the 65-footer Selden III and can accomodate nine cars and 49 passengers. Though the trip is only about four minutes long, it's scenic and historic. It's $4 per vehicle on weekdays and $5 on the weekends, but walking on only costs $2. See its website for hours of operation.
- Cornwall Bridge: The red, covered bridge reaches across the Housetonic River between Sharon and West Cornwall. It will hit its 150th anniversary next year – it was built in 1864, painted red in 1957 and has held up against floods, ice and traffic ever since. See this website for more information about the bridge.
- Hammonasset Beach: The beach opened in 1919 after Connecticut paid nearly $131,000 for 75 parcels of Madison land, including 565 acres near or adjacent to the shore. Now, the beach has 919 acres, more than 2 miles of beach. See the website for details about parking.
- Gillette Castle: Stage actor William Gillette, best known for his part as Sherlock Holmes, built the castle in 1919 on more than 100 acres above the Connecticut River. There are trails and a three-mile railroad on the property as well. The castle has 24 rooms with parapets, a turret, a tower, secret rooms, 47 interior oak doors of various sizes and a dining table on tracks. For more information about the castle, see its website.