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The seaport of Portland is Maine’s largest urban area. Perched on Casco Bay, it’s home to many island and coastal communities. The city is known as a cultural, dining and shopping destination, but you'll also find walking and biking trails as well as a beach. You can also tour the Portland Observatory—the only remaining historic signal tower in the nation—or take a Great Portland Landmarks self-guided walking tour of Portland's four major historic districts. You can also attend a number of fairs and festivals throughout the year, including:

  • Maine Jewish Film Festival (March)
  • Old Port Festival (June)
  • Portland Chamber Music Festival (August)
  • Harvest on the Harbor Food & Wine Festival (October)
  • Tree Lighting in Monument Square (November)

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