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Visiting Maine in October - just had a few questions!

Buffalo, New York
3 posts
Visiting Maine in October - just had a few questions!

In Portland, what is the weather usually like in late October (that is when my stay begins; its end date is the first few days of November)?

How spread out is Portland? Depending on where you want to go (say, somewhere within the downtown district), is it reasonable to take a pleasant walk out to reach your destination?

Aside from bars and restaurants, what attractions must a visitor to Portland see before they leave? My friend and I are particularly interested in the arts, museums, historic sites, etc. Would any locals happen to know of worthwhile attractions that are a little difficult to find/not exactly popular and thus not often found as recommended spots on travel guides? If so, what are they?

Is there enough to do in Portland alone for a few days? I know it's one of the smaller cities in America, but I've been looking over Google Maps/Street View and the main tourist areas, those being Old Town Portland and the Arts District, seem to be about the size of the downtown district of my small town. If you stray outside of them both, is there anything else in Portland to hold the interest of a visitor?

I'll take as much information as the community here can offer.


Bar Harbor, Maine
Destination Expert
for Bar Harbor, Acadia National Park
Level Contributor
3,947 posts
13 reviews
1. Re: Visiting Maine in October - just had a few questions!

I don't qualify as a local but I am a fairly frequent visitor. Some of the questions must await others.

Staying in the Old Port area puts you in easy strolling distance of the waterfront, the shops, and the restaurants. Also, there is easy access to Casco Bay Ferries which serve the islands in the bay. The about half-day mail-boat run is a great way to see the bay and the islands.

If you enjoy walking, check out the Portland Trails site:


There are 31 (maybe more, now) trails of varying length. The Eastern Prom and Back Cove loop is a nice one.

Portland, Maine...
Level Contributor
24 posts
8 reviews
2. Re: Visiting Maine in October - just had a few questions!

If you are interested in historical sites and the outdoors, check out www.portcityrunningtours.com.

The Lucky Catch is a great experience. Also, for food/drinks, you must check out J's Oyster Bar. It's a fun place that a lot of people I've had come visit like.

Southern Maine
Destination Expert
for Maine
Level Contributor
4,279 posts
11 reviews
3. Re: Visiting Maine in October - just had a few questions!

The Portland Museum of Art is definitely worth a visit. It's free on Friday nights after 5:00:


I'm not sure of your exact dates, but Portland also hosts a First Friday Art Walk:


Three places that combine your love of history and museums are:




Level Contributor
570 posts
294 reviews
4. Re: Visiting Maine in October - just had a few questions!

You might try visiting Peaks Island. A short ferry ride brings you to this beautiful litlle island. Walk the 4 mile loop and have lunch in the Inn on Peaks. A great way to spend a nice morning or afternoon.

5. Re: Visiting Maine in October - just had a few questions!

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