If you are looking for things to do in Portland, Maine this weekend and beyond, you will not be disappointed. It is a packed calendar, so whether you are in the mood for an epic Oktoberfest bar crawl, live music, local history, or fall flavor, Portland’s got it covered.

Today kicks off with Oktoberfest Portland style. According to Eventbrite, the Official Oktoberfest Bar Crawl takes over downtown starting at 4 PM today, Saturday, September 27. You can check in at Mathew’s on Free Street, grab an official wristband, and immerse yourself in a tour of Portland’s best bars and venues with exclusive drink specials, live music, DJs, and an after-party. That is not all—each location offers themed perks and the digital map makes hopping between spots easy. Remember, you have to be 21 and over with a valid ID for this one, and the party goes until 11 PM.

Craving more live music? The Portland Old Port Weekend Guide highlights several shows all over the city. Look for local favorites and cover bands, including an outdoor set with Keanu and Vinyl Tap from noon to 5 PM on Sunday. If you want a laugh, check out the comedy acts rotating through downtown venues. For a quieter vibe, the Maine Historical Society offers exhibit walk-throughs after hours several nights this week, perfect for history buffs or a mellow evening.

Fall is in full swing and that means it’s prime time for festivals. Flannel Fest runs September 27 and 28, not far from town, and is all about Maine pride with artists, makers, and local food and drink wherever you look. For those who love a classic autumn adventure, Portland’s area corn mazes and pumpkin patches are bustling right now and easy to reach by car or Uber.

If you are up early, Portland’s waterfront shines in the fall. You can set sail on a whale-watching tour any morning or evening. Kayak tours across Casco Bay are perfect for the active crowd, and a city and lighthouse cruise or tour is always memorable. The Greater Portland Maine Events Calendar suggests trivia nights along the waterfront, book clubs with snacks, and walking tours revealing the hidden stories of Black Portlanders.

This week, keep an eye out for pop-up ethnic food tours showcasing Portland’s renowned restaurant scene, and guided tastings at local breweries. And for something totally unique, the Kotzschmar Organ inside Merrill Auditorium has a behind-the-scenes tour and live demonstration—music lovers, this one is unmissable.

Whether you’re here to dance, explore, eat, or just relax, there’s something special for every listener. Thanks for tuning in, and don’t forget to subscribe. This has been a quiet please production, for more check out quiet please dot ai.

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