Parkside Travel Guide
Portland
Popular places to visit
State Theatre
The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.
Portland Museum of Art
Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.
East End Beach
Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.
University of Southern Maine
Enjoy the student vibe at University of Southern Maine as part of your travels around Portland. Stroll along the seaside or attend a sporting event in the area.
Eastern Promenade
Built on an old rail corridor along the easternmost portion of Portland’s peninsula, this waterfront trail offers stunning views of the harbor and Atlantic Ocean.
Portland Observatory
After visiting Portland Observatory, make a plan to see the other sights and activities in Portland. Stroll along the area's seaside or experience its entertainment choices.
Things to do
The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local
Ultimate Portland Self-Guided Driving GPS Audio Tour
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
Portland Maine Self-Guided Driving & Walking Audio Tour Bundle
The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local
Ultimate Portland Self-Guided Driving GPS Audio Tour
Top hotels in Parkside
Longfellow Hotel
"Clean, comfortable rooms. Hotel does have a few food options near by but car service was wonderful as it’s not near most of the restaurants & shops. Overall great hotel!"
Reviewed on 17 May 2026
The Francis
"Great location, comfortable bed, charming property, friendly and helpful staff."
Reviewed on 1 May 2026
Portland Harbor Hotel
"Wonderful hotel with clean rooms, easy valet parking, and a great location. We loved the small area right off of the elevator on our floor which provided water, coffee, and pastries for use in the mornings."
Reviewed on 21 May 2026
Portland Regency Hotel & Spa
"We’ve stayed at this hotel 5 times now and have always enjoyed the historic charm and location. Check-in during this stay went smoothly, however we were disappointed when we arrived to find the toilet in our room was dirty. We also asked the front desk if the TVs allowed streaming services like Netflix ..."
Reviewed on 20 May 2026
Cambria Hotel Portland Downtown-Old Port
"Clean room, nice location. Wish the tv was a smart tv, and found the $25/room sort of annoying since the restaurant on property was understaffed. But overall we enjoyed it."
Reviewed on 21 May 2026
HomeAwhile
"Honestly happily surprised at the room for the price. The staff was communicative and kind and the room was clean and spacious. I’d definitely come back."
Reviewed on 21 May 2026
Other neighbourhoods around Parkside
Portland Arts District
The ample dining options and captivating waterfront views are top of the list for many visitors to Portland Arts District. A stop by Cross Insurance Arena or Portland Museum of Art might round out your trip.
West End
If you're spending some time in West End, Victoria Mansion and Portland Fire Museum are top sights worth seeing.
West Bayside
When in West Bayside, you can plan a visit to Bayside Bowl and Merrill Auditorium, some noteworthy sights in the nearby area.
Valley Street
While visiting Valley Street, you might make a stop by sights like Hadlock Field and Fitzpatrick Stadium.
Oakdale
While Oakdale may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Hadlock Field and Bayside Bowl.
Downtown Portland
A noteworthy feature of Downtown Portland is its captivating waterfront views. While you're in town, be sure to stop and check out Cross Insurance Arena and Merrill Auditorium.
