2025 Compare Cities Overview:
Chestertown, MD vs Portland, ME

Are people in Portland older or younger than people in Chestertown?
- The Median Age in Portland is 2.2 years younger than in Chestertown.

Are housing costs cheaper in Portland or Chestertown?
- Portland housing costs are 43.7% more expensive than Chestertown housing costs.

Which city has a longer commute, Portland or Chestertown?
- The average commute for residents of Portland is 7.6 minutes shorter than it is for residents of Chestertown.

Things to do in Chestertown?
Chestertown, MD is a charming and vibrant small town nestled in the beautiful Chester River Valley. It has a rich history as one of the oldest towns in Maryland, established in 1706. With its cobblestone streets and historic buildings, it is a pleasure to explore the sights of Chestertown. The downtown area offers plenty of shops, restaurants and cultural attractions to keep you entertained. During the summer months there are an abundance of activities such as farmers markets and festivals to experience. The locals here are friendly and welcoming, making it easy to feel at home when living in Chestertown. Furthermore, with its close proximity to Washington D.C., Baltimore and Philadelphia, Chestertown is an ideal location for commuters looking for a quiet place to call home.

Things to do in Portland?
Portland, Maine is a picturesque coastal city located on the shores of Casco Bay. This historic town features an array of attractions for visitors to explore such as the fascinating Victoria Mansion or the charming Portland Lighthouse. Residents here also enjoy plenty of outdoor activities at Back Cove or Willard Beach. With its top-rated schools, thriving businesses, and wide selection of recreational opportunities, it's no wonder why so many people choose to make Portland their home.