Trips & Travel

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OLLI goes on several regional excursions throughout the year to local points of interest (focused on Maine, New Hampshire, or Massachusetts) plus up to two international trips each year, often in May or November.

Upcoming OLLI excursions will be announced soon!

Registering for local excursions

1. Sign in as a current member.
2. Select the ‘Trips and Travel’ category.
3. Click on the date to add the trip to your Cart and head to checkout!

Registration for International trips is not online
Details will be shared with members via the newsletter or other announcements.
(Registration for international travel is in-person, first-come, first-served!)

Staycation - “The Trail to Freedom” Walking Tour
In-Person
Fee: $32.00
Dates: 8/12/2026 - 8/12/2026
Times: 9:00 AM - 11:00 AM
Days: W
Sessions: 1
Building: Off Site
Room: Portland
Instructor: Roberta Muse
Seats available: 8

On a leisurely walking tour of Underground Railroad landmarks and the Eastern Cemetery, learn about important people and events inPortland’s Black History and Maine’scontributions to emancipation. BruceGarrow returns as our guide for thisnew tour.

Rain date: Thursday, 8/13.

Location to be determined.

Staycation - Maine Audubon
In-Person
Fee: $15.00
Dates: 7/8/2026 - 7/8/2026
Times: 10:00 AM - 12:00 PM
Days: W
Sessions: 1
Building: Maine Audubon (opens in new tab)
Room:
Instructor: Christine Milligan-Brown
Seats available: 13

We’re looking forward to an upcoming visit to Maine Audubon in Falmouth for an informative talk on birdwatching and tips for spotting local species. Use of binoculars, spotting scopes, and useful apps will be included. After the presentation, a guided tour of the scenic trails will give us the chance to explore diverse habitats up close and put our new skills into practice. Picnic tables are available for your picnic lunches conveniently near Audubon’s active birdfeeders. Meet at Maine Audubon, Falmouth.

Staycation - Maine Jewish Museum
In-Person
Fee: $7.00
Dates: 7/22/2026 - 7/22/2026
Times: 11:00 AM - 1:00 PM
Days: W
Sessions: 1
Building: Maine Jewish Museum (opens in new tab)
Room:
Instructor: Christine Milligan-Brown, Faye Gmeiner
Seats available: 5

Join us for a visit to the Maine Jewish Museum in Portland followed by a walking tour of the India Street area. Learn about Maine’s Jewish heritage and visit their rotating art exhibition, in this beautifully restored synagogue. Then explore the quiet charm of the East End while taking a meaningful dive into local history, art, and culture.

Meet at the Maine Jewish Museum, Portland.

Staycation - Pineland Farms
In-Person
Fee: $19.00
Dates: 8/5/2026 - 8/5/2026
Times: 10:00 AM - 12:30 PM
Days: W
Sessions: 1
Building: Pineland Farms (opens in new tab)
Room:
Instructor: Marvin Druker
Seats available: 15

Located in the rolling hills of New Gloucester, Pineland Farms is a working farm, vibrant business campus, and year-round educational and recreational destination for visitors of all ages. During our visit, we will board the Pineland trolley for a guided tour of the historic campus, the beautiful perennial gardens, and the farm, where we will meet a variety of animals. After the tour, you are welcome to enjoy lunch on your own at the Pineland Café or browse the Farm Market for fresh produce, meats, and local goods.

Meet at Pineland Farms, New Gloucester.

Staycation - Seashore Trolley Museum
In-Person
Fee: $19.00
Dates: 7/29/2026 - 7/29/2026
Times: 9:30 AM - 11:30 AM
Days: W
Sessions: 1
Building: Seashore Trolley Museum (opens in new tab)
Room:
Instructor: Faye Gmeiner
Seats available: 17

Seashore Trolley Museum is the first (1939) and largest electric railway museum in the world, with more than 250 vehicles from almost every major city in the U.S. that had a streetcar system. Join us as we ride three miles in a restored trolley from the early 1900s and take a walking tour of the restoration barn, car houses, and grounds with our docent.

Note: the museum has a mobilift for access to the trolley if needed.

Meet at the Seashore Trolley Museum, Kennebunkport.

Staycation - The Portland Museum of Art & The Winslow Homer Studio
Fee: $67.00
Item Number: SU26TAT101101
Dates: 7/16/2026 - 7/16/2026
Times: 10:00 AM - 1:00 PM
Days: Th
Sessions: 1
Building: Portland Museum of Art (opens in new tab)
Room:
Instructor: Bruce Smith

THIS CLASS IS FULL. Please click the "Add to Waitlist" button below.

A small group of 12 members will meet at the Portland Museum of Art and then be taken to Winslow Homer’s Studio where you can step into the artist’s life. New interactive displays, soundscapes, and lighting will provide context for his creations and the nearby landscape. The group will return to the PMA for free time in the galleries or lunch on your own.

Meet at the Portland Museum of Art, Portland.

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