With its beautiful lighthouses, award-winning lobster rolls, rich historic district, world-class dining scene, and striking scenery, I am adding Portland to the list of cities that are a must-see in the Northeast of the United States!

Whether you are looking to take a vacation with friends, family, or by yourself to Portland, here is a list of fun things to do when you visit Portland!

For those of you familiar with Maine, Portland is located 30 miles north of Kennebunkport, another coastal town in Maine that I recommend you visit.

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Very Best Things To Do in Portland, Maine

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1. Visit Portland Breakwater Lighthouse (Bug Light Park)

Bug Light Park is one of my favorite spots in Portland!

Originally constructed in 1855, the new 26 ft lighthouse resembles a 4th century Greek monument that was inspired by the Choragic Monument of Lysicrates in Athens. The light was restored in 1989 and was reactivated in 2002.

The surrounding park is the perfect place for a waterside walk, and if you visit during sunset you might catch one of the prettiest pink sunsets you’ll ever see.

This gem was added to the National Register of Historic Places in 1973 and memorializes the shipbuilding efforts of World War II.

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Here’s a popular bicycle tour that takes you to the lighthouses:

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This park offers free parking. We stopped here the night we arrived in Portland. I captured these photos at 8:02 PM on July 30th!

How to get there: Bug Light, S Portland Greenbelt Pathway, South Portland, ME 04106

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2. Climb the Portland Observatory

If you’d like to admire Portland from above, then the Portland Observatory is for you!

The 86-foot high observatory is a historic maritime signal tower that was built in 1807 at the direction of sea captain-turned-entrepreneur Captain Lemuel Moody (1768-1846). It is the only known surviving tower of its type in the United States.

At the time, ships entering the harbor could not be seen from the docks of Portland until they rounded the point of land at Spring Point Ledge and were almost in the harbor. Moody identified incoming vessels with his powerful telescope at the top of the tower.

The Observatory remained a working marine signal tower run by the Moody family until 1923 when the invention of the two-way radio made it obsolete. 

I highly recommend the guided tour! My husband was pleasantly surprised – he loved learning the history of the builder, the physical structure of the tower, and the impact it had on Portland’s harbor. We also thought the views from the top were fantastic!

The tour lasts 45 minutes, you will climb 103 steps, and once you reach the top you will enjoy a 360-degree panoramic view of Portland. The breeze blowing through the open windows made the climb comfortable. The tour stopped on each level for the interesting exhibits, and to allow everyone to sit or move upstairs at a reasonable pace. Tickets are $10 for adults and $5 for kids ages 6-17.

How to get there: Portland Observatory, 138 Congress St, Portland, ME 04101

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SHOP: Cleobella Eyelet Dress

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3. Tour the Historic Victoria Mansion

Victoria Mansion was built between 1858 and 1860 as a summer home for two people, Ruggles Sylvester Morse and his wife Olive. When Morse died in 1893, his wife sold the house with most of its furnishings to J.R. Libby, a prominent dry goods merchant.  The Libbys occupied the mansion until 1929.

The house has been open to the public as a museum since 1941 and was named a National Historic Landmark in 1971.

Don’t miss this gem! The mansion is one of the finest examples of the Italian Villa style in the United States. It is strategically located near the city’s earliest gas and sewer lines, and the house had hot and cold running water.

I loved stepping back in time, and being able to see 90% of the original interiors of the house! The original wall paintings by the Italian-born artist Giuseppe Guidicini, a master of the trompe l’oeil (“fool the eye”) style, make the surfaces in the house appear to be three-dimensional and will make you look twice! The mansion’s parlor and reception suite are breathtaking.

The guided tour lasts 45 minutes. Tickets are $16 for adults and $5 for kids ages 6-17.

VIDEO: See the video I made after touring Victoria Mansion here.

How to get there: Victoria Mansion, 109 Danforth St, Portland, ME 04101

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Shop: Cleobella Dress

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4. See the Portland Head Light

The Portland Head Lighthouse is Maine’s oldest lighthouse and the most photographed lighthouse in the United States!

Construction began in 1787 at the directive of George Washington and was completed in 1791.

How to get there: Portland Head Light, 12 Captain Strout Cir, Cape Elizabeth, ME 04107

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This is another popular bicycle tour, that includes a complimentary lobster roll at an award-winning food truck:

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5. Walk around the Arts District & Downtown Portland

The Arts District is a section of downtown Portland designated in 1995 to promote the cultural community of the city.  It covers a large part of Upper Congress Street towards the West End.

Right behind that green clock on Monument Square, you will find Hifi Donuts, a neighborhood spot in a vintage setting where we grabbed artisanal donuts & lattes one early morning.

In these areas, you will find many coffee shops, bars, restaurants, art galleries, a theater company, and museums. Maine College of Art (MECA) and the Portland Museum of Art are located here as well.

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6. Bike around Spring Point Ledge Lighthouse

A caisson-style lighthouse located in South Portland that was first lit in 1897 to help watercraft safely navigate Casco Bay!

We enjoyed walking around the trails that surround this lighthouse during sunset. We saw lots of people letting their dogs play in the water.

The views were picturesque and magnificent all around.

How to get there: Spring Point Ledge Lighthouse, 2 Fort Rd, South Portland, ME 04106

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7. Try Honey Wine at Maine Mead Works

Maine Mead Works is a winery that specializes in honey wine. The winery’s brand HoneyMaker is offered in a variety of year-round and seasonal styles and is all hand-crafted in Maine using 100% wildflower honey.

We visited the tasting room at Maine Mead Works and enjoyed a flight of four different meads: lavender lemonade, cranberry, blackberry lavender mint, and dry. These flavors were so good.

How to get there: Maine Mead Works, 51 Washington Ave, Portland, ME 04101

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8. Enjoy Dinner at Scales on the Maine Wharf

Scales is a traditional New England restaurant that offers lobster, seafood, and a raw bar in an elegant setting on the Maine Wharf, on Portland’ Maine’s Historic Waterfront.

We loved our appetizers and dishes: anadama bread, green salad, Maine clam chowder, warm buttered lobster roll, and grilled Maine bluefin tuna.

We also ordered a mint chip frappe to-go! Be sure to make your reservation weeks in advance!

How to get there: Scales Restaurant, 68 Commercial St, Portland, ME 04101

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9. Try the Mini Donuts at Eighty 8 Donuts

Eighty 8 Donuts was highly recommended to us by locals we met during our first night in Portland. When you visit Portland, trying these donuts is a must!

We ordered a box of ‘Specialty Bites’ and the taste was divine. The flavors included: Bamm Bamm (fruity pebbles topped donut), Homer (strawberry glaze with rainbow sprinkles), 007 (maple icing with bourbon cream and candied bacon), Cookies & Cream (cookie on a donut), Boston Cream (chocolate icing with Bavarian cream) and Lemon Zinger (lemon glaze with a raspberry center).

This flavorful walking tour takes you to donut shops in Portland’s Old Port:

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Eighty 8 Donuts also has a location at the base lodge of Sugarloaf Mountain in Carrabassett Valley and a donut truck that is based in Portland, Maine.

How to get there: Eighty 8 Donuts, 225 Federal St, Portland, ME 04101

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10. Grab a Lobster Roll at The Highroller Lobster Co.

Portland has some of the best lobster you will ever find, and plenty of places offering delicious lobster rolls.

We decided to check out The Highroller Lobster Co., a neighborhood diner that serves a full menu of lobstery options. My husband does not eat shellfish, so after I finished my lobster roll we walked 140 feet to Crispy Gai where he ordered fried chicken.

Luke’s Lobster is one of the favorites among tourists. You can find this spot directly on the working waterfront, off the Portland Pier, in the heart of the Old Port.

How to get there: Highroller Lobster Co., 104 Exchange St, Portland, ME 04101

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11. ViA VECCHiA

Via VECCHiA is a trendy restaurant located in the heart of the Old Port in a historic brick and ivy-covered building overlooking cobblestone streets. 

How could I not order the Florentina Spritz?!

Be sure to make a reservation in advance because this restaurant fills up quickly! My only regret is not coming here twice!

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12. Have Brunch at Bayside American Cafe

This well-known breakfast spot has been a local landmark since 1990. Their famous brunch menu features breakfast, lunch and specialty brunch items such as Maine lobster eggs benedict, homemade corned beef hash, as well as pancakes and French toasts served with 100% local Maine maple syrup.

Because we visited in July, the patio and deck were open for dining. Brunch is served from 7 AM – 2 PM, Wednesday – Monday.

How to get there: Bayside American Cafe, 98 Portland St, Portland, ME 04101

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What surprised me the most about Portland was the fantastic food! We are already looking forward to visiting Portland again in the near future.

I hope today’s post helps you plan a trip to this must-see destination in Maine!

Keep reading to see more fun things that you can add to your Portland itinerary!

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MAP OF PORTLAND MAINE

In the map below I marked the location of the best things to do in Portland ME:

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How many days do I need in Portland, Maine?

2-3 days in Portland, Maine is the perfect amount of time to discover the city’s history and enjoy some of the best craft brews and bites you’ll ever have.

What is the best time of year to visit Portland, Maine?

The best time to visit Portland is June – September.

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More Things To Do in Portland

Here are popular activities to add to your itinerary:

• Lighthouse Cruise in Portland
• Portland Museum of Art
• Visit Peaks Island
• Eastern Promenade Trail (2.1 miles long)
• Allagash Brewing Company
• Austin Street Brewery

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BEST PLACES TO STAY

We needed a pet-friendly hotel and stayed at Westin Portland Harborview where our dogs stayed for free. We liked the location of this hotel, it was in the heart of Downtown Portland.

Here are more great options, click on any hotel below to see the rates:

• The Press Hotel, Autograph Collection
• Portland Harbor Hotel
• Canopy By Hilton Portland Waterfront
• Blind Tiger Guest House
• The Chadwick Bed & Breakfast
• AC Hotel by Marriott Portland Downtown
• The Francis

RELATED ARTICLE:

Bring Your Pets on Vacation to these Amazing Hotels

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MORE CITIES YOU WILL ENJOY

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• FLORIDA: St. Augustine: 2-Day Itinerary
• VERMONT: 2 Days in Woodstock & Where To Stay
• GEORGIA: 5 Hours in Savannah

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