10 Fun Things to Do in Portland, Maine

fun things to do in Portland, Maine

Looking for great activities near York? You won’t have to look any further than all the fun things to do in Portland, Maine. Whether you’re interested in art, history, great food, or shopping, we can guarantee that you won’t be disappointed. While it’s impossible to pick our favorite, we have compiled a list of the best things to do in Portland, Maine. You’ve got to check these out during your visit!

For even more recommendations on the best things to do in Portland, Maine, download our free Maine Vacation Guide! Get ready for your Dockside Guest Quarters adventure!

10 of the Most Fun Things to Do in Portland, Maine

Not sure what to do in Portland? The largest city in Maine has plenty of things to do, including some of the most famous historical sites in Maine. Check out our list of our favorite things to do on a day trip up to Portland, Maine!

1. Food Tours

Take one of the many foodie tours around Portland, Maine. These tours will take you to some of the best restaurants in Portland, which is known for its great food. Sample some of the best lobster restaurants or try a cooking with friends tour. There are many different options to fit any culinary taste and can help you get to know the city even better, plus you’ll get to have some of the best food Portland has to offer!

2. Beer Tastings

Head to one of the many great breweries in Portland, Maine or try the Maine Brew Bus which is a great experience for those over the age of 21. Jump on the Maine Brew Bus and tour the local craft beer scene. Try great local brews while riding in the safety and comfort of the Maine Brew Bus. Enjoy a tour with information, snacks, trivia and delicious beers.

3. Portland Sea Dogs

The Portland Sea Dogs are a Double-A affiliate of the Boston Red Sox and play their games at Hadlock Field in Portland. The Sea Dogs have several home games through the months of July and August with plenty of chances to see them in action. The Sea Dogs provide a great environment to enjoy baseball and have fun with the whole family. Plus, you’ll have a chance to see future Red Sox players before they hit the big leagues!

4. Boat Tours

Take a boat tour from Portland, Maine and experience the sea life of New England. Or head over to Casco Bay and take a trip on the Casco Bay Ferry to Peaks Island, which is just a short 17-minute ferry ride. Enjoy the amazing scenery before heading to this family-friendly scenic destination. Hop on a golf cart and tour the island, enjoy a meal next to the ocean, rent a kayak and head out in the bay, tour the historical sites or just relax.

5. Portland Head Light

One of the most iconic things to do in Portland, Maine is a visit to the Portland Head Lighthouse. It was commissioned by President George Washington in 1791 and was the first lighthouse in the United States. It is reported to be the most photographed lighthouse in the world, and certainly the most famous of the lighthouses in Maine. There are few sites more iconic than this one and should be visited by anyone in Portland.

6. Portland Observatory

A historic maritime signal tower in the Munjoy Hill neighborhood of Portland, the Portland Observatory was constructed in 1807. It is the only surviving structure of its type in the United States!

7. Eastern Promenade

In the same neighborhood as the Portland Observatory, the Eastern Promenade follows an old rail track and is a beautiful walking trail along the waterfront. This little reserve is beautiful with scenic views of the water as well as play areas, basketball and tennis courts.

8. Maine Narrow Gauge Railroad Museum

Train fanatics need to include a visit to the Maine Narrow Gauge Railroad Museum while in our beautiful state. This museum features various historic equipment used to traverse the narrow 2-foot tracks that used to cross Maine in the 19th and 20th Centuries.

9. State Theatre of Portland

Fans of historic architecture will love to visit the State Theatre in downtown Portland, which features both Moorish and Art Deco features. First opened in 1929, this theatre was recently reopened with thousands more seating than the original plan, and still puts on plenty of shows and plays. Another fantastic theater to explore in the area is the Music Hall in Portsmouth, New Hampshire.

10. Merrill Auditorium

Another opportunity to enjoy some plays in Portland, Maine, is the historic Merrill Auditorium. Built in 1911 in downtown Portland on the eastern campus of the Portland City Hall near the Old Port, the Merrill Auditorium is where you’ll find shows, concerts, and plays by the Portland Ovations and the Portland Symphony Orchestra.

Stay in Nearby York

When enjoying the many fun things in Portland, make sure to book a stay at Dockside Guest Quarters. Not only do the accommodations offer timeless style combined with modern comforts, but when you stay you also get breakfast from our bountiful buffet each morning, ensuring that your days will start off on the right note. Our Dockside Restaurant is perfect for a great meal. For an all-around good time in coastal Maine, stay at Dockside Guest Quarters. Unlike hotels in Portland, our Maine lodging is quiet, and includes fantastic views of the York harbor. We’re also a perfect location from which to explore Portland, the Kennebunks, Kittery, Ogunquit, and Portsmouth, New Hampshire! We can’t wait to see you soon!