Chestertown travel guide
Chestertown Tourism | Chestertown Guide
You're Going to Love Chestertown
With a population of 5,252, Chestertown is a must-see destination in Maryland, United States. It is among the most popular tourist destinations in the country. Consider staying at least one whole day in Chestertown to see all of its attractions.
Where to Eat in Chestertown
If you’re looking for affordable options, Casa Carmen (312 Cannon St) and The Retriever Bar & The Decoy Bottle Shop (337 1/2 High St) are great picks.
When to visit Chestertown
Looking for warm weather? Then head to Chestertown in July, when the average temperature is 77 °F, and the highest can go up to 87.8 °F. The coldest month, on the other hand, is January, when it can get as cold as 24.8 °F, with an average temperature of 33.8 °F. You’re likely to see more rain in July, when precipitation is around 4.2″. In contrast, February is usually the driest month of the year in Chestertown, with an average rainfall of 3″.
How to Get to Chestertown
Plane
Although Chestertown doesn’t have its own airport, you can fly to Greater Wilmington (ILG), which is located 41 miles from Chestertown. Philadelphia Airport is the most popular, with regular flights from American Airlines, Air France, ITA Airways and other airlines departing from the United States. The shortest domestic flight to Chestertown departs from Fort Lauderdale and takes around 2h 35m.
Train
Amtrak is the only carrier operating train routes to Chestertown. The train journey from Chestertown to Baltimore takes 0h 29m and costs around $11 for a one-way ticket. When coming by train from Philadelphia, expect to pay about $11 for a 1h 56m trip.
Car
Another option to get to Chestertown is to pick up a car rental from New York, which is about 153 miles from Chestertown. You’ll find branches of Sixt and Kyte, among others, in New York.
Bus
Several bus lines operate bus routes to Chestertown, including Megabus, Peter Pan Bus Lines and CoachRun. From Philadelphia, the bus ride to Chestertown takes 170 miles and will cost you around $20. From New York, the ticket costs about $12 for a journey of 275 miles.
Airlines serving Chestertown
Where to stay in Chestertown
Average rates range from around $119 per night for a double room in a 3-star hotel to $312 and up for a 5-star experience.
Where to stay in popular areas of Chestertown
Most booked hotels in Chestertown
Renting a car in Chestertown
Renting a car in Chestertown costs $66 per day, on average.
It’s generally cheaper to rent your vehicle outside the airport: locations in the city are around 12% cheaper than airport locations in Chestertown.
Expect to pay $3.90 per gallon in Chestertown (average price from the past 30 days). Depending on the size of your rental car, filling up the tank will cost between $46.79 and $62.38.