Top 10 things to do in Portland, Maine this fall

May 28

Whether you're planning a staycation or a vacation, immerse yourself in the finest autumn activities that the Portland, Maine area has to offer. Begin your journey with a delightful stay at either the Portland Harbor Hotel or Cambria Portland Downtown-Old Port old port district of Portland, celebrated for its cobblestone streets, delightful boutiques, and captivating waterfront vistas. The vibrant hues of fall foliage enhance the area's already picturesque charm.

Portland Head Light: Visit the iconic Portland Head Light in Cape Elizabeth, just a short drive from the hotel. This historic lighthouse offers stunning ocean views and is especially beautiful during the fall.
Fall Foliage Tours: Take a scenic drive along Route 302 or Route 1 to witness the breathtaking fall foliage in Maine. You can also consider joining a guided fall foliage tour for a more immersive experience.
Hiking: Explore nearby parks and trails, such as Bradbury Mountain State Park, Wolfe's Neck Woods State Park, or Great Diamond Island, which all offer fantastic hiking opportunities amidst fall foliage.
Apple & Pumpkin Picking: Head to a local orchard like Sweetser's Apple Barrel and Orchards or Giles Family Farm to pick your own apples, a classic fall activity.
Our Top Picks:
- Sweetser’s Apple Barrel and Orchards |Cumberland, Maine
- Hansel’s Orchard | North Yarmouth, M.E.
- Orchard Ridge Farm | Gorham, M.E.
- Randall Orchards | Gorham, M.E.
- Thompson’s Orchard | New Gloucester, ME

5. Wine Tasting: Visit local wineries and vineyards like Cellardoor Winery or Savage Oakes Vineyard & Winery for wine tastings and beautiful vineyard views.

6. Brewery Tours: Portland is known for its craft beer scene. Take a brewery tour and sample some seasonal brews at popular breweries.

Also, Try Seasonal Cocktails & Coffee:

Harbor Bistro + Terrace | Portland, M.E.

Alto Terrace Bar + Kitchen | Portland, M.E.

Bard Coffee | Portland, M.E.

Coffee By Design | Portland, M.E.

Tandem Coffee | Portland, M.E.

7. Fall Festivals: Check the local event calendar for fall festivals, farmers' markets, and art fairs happening in the area. The Portland Harvest on the Harbor is a notable food and wine festival that takes place in the fall.

Upcoming Events:

Freeport Fall Festival | October 6-8, 2023
Cumberland Fair | September 24-30, 2023
Harvest on the Harbor | October 25-28, 2023
Pineland Farms Harvest Festival | September 30, 2023

8. Leaf Peeping Cruises: Consider a scenic cruise on Casco Bay to see the fall foliage from a different perspective. Some boat tours even offer narrated tours to educate you about the area's history and natural beauty.

9. Museum Visits: Explore Portland's cultural side by visiting museums like the Portland Museum of Art or the Maine Historical Society. They often feature special exhibitions and events during the fall.

10. Best Seasonal Donuts: Visit local farms and shops to experience the best tastes of fall!

Our Top Picks: