A complete guide of the things to do in Portland, Maine. The city of under 70,000 people feels like a city and a small town all at the same time.

If you fly into Maine, you will likely be landing in Maine. Portland is a city worth exploring and it can be seen over a weekend. From Portland, you can easily drive along Maine’s coast to places like Acadia National Park.

Things to do in Portland, Maine:

Table of Contents

I have broken this list down into several different categories to make it easy for you to find what you are looking for. You will find lists of tours, lighthouses, landmarks, parks, shops, music and theater, breweries, restaurants, bars, museums, and annual events. It is a complete guide of things to do in Portland, Maine.

Portland Maine Tours:

There are so many ways to explore Portland! Sail, cruise, or paddle in Casco Bay, bike to lighthouses, or walk between restaurants. Most of these tours are only available between May and October.

Sail on a Schooner

Portland Schooner Company has three different schooners that run two-hour sails on Casco Bay. The small fleet of boats are all listed on the National Register of Historic Places, and they were built in 1912, 1924, and 1931.

Kayak and SUP Tours

Portland Paddle runs a mix of sightseeing tours. You can choose from a sunset paddle, a visit to Fort Gorges, a full day Lighthouse and Fort Tour, a moonlight paddle.

Casco Bay Ferry Ride

A variety of ferries run from Portland to the islands in Casco Bay. Hop on the mailboat run, a sunset cruise, or a music cruise.

Go on a Whalewatch

The Gulf of Maine is a feeding ground for humpback whales, and going on a whale watch is one of the most popular things to do in Portland. There are several tour companies offering whale watches in Portland.

Take a Lobster Boat Tour

You can get a behind the scenes look at the lobstering industry aboard the Lucky Catch. Guests get to help haul traps during this 90-minute tour that also takes you past lighthouses and historic sites.

Maine Duck Tours

Inspired by the similar tours in Boston, guests on this tour board an amphibious vehicle to explore the history of Portland by land and sea.

Maine Foodie Tours

This company offers a variety of food tours, including a Lobster Crawl, a progressive dinner, a top restaurant tour, and a tour that blends art, culture, and food. Some tours are seasonal, while others are offered all year.

Discovery Land and Sea Tours

Tour Portland by trolley, boat, or both. This company offers tours to see lighthouses as well as tours of downtown Portland.

Bike Tours:

Summer Feet Cycling runs a half day bike tour that will take you to five lighthouses!

Maine Brew Bus

This tour company will take you to multiple breweries in one day. Book in advance, it’s become a popular attraction.

Portland Lighthouses:

Portland Head Light

Don’t let the name confuse you. Portland Head Light is actually in Cape Elizabeth, just south of Portland. It is Maine’s most famous lighthouse, stands 80 feet tall, dates back to 1791, and is Maine’s oldest lighthouse. You can tour this lighthouse and see the original keeper’s quarters. During the summer months, a popular lobster roll truck is parked nearby.

Bug Light (Portland Breakwater Light)

Located at the end of the breakwater in Portland Harbor, Bug Light is inside Bug Light Park. It stands just 26 feet tall. It isn’t open for tours, but it is a good photo opportunity.

Spring Point Ledge Light

This lighthouse is beside Fort Preble and is open to visitors during the summers. Visitors to the lighthouse also get a great view of Portland from across the water.

Ram Island Ledge Light

A lighthouse on a small island in Casco Bay that marks the location of rocks. The island and the lighthouse are not open to the public but they can be seen from Portland Head Light.

Portland Landmarks:

Portland Observatory

This landmark is known for its wonderful views of Portland. Originally built in 1807, Portland Observatory is the oldest maritime signal tower in the country. It is open from May until October, just be prepared to climb some stairs.

Victoria Mansion in Portland

One of Portland’s grandest homes, Victoria Mansion was built in 1858 and is an example of Vill Style architecture. Built as a private residence, it was technologically advanced for its time with conveniences like hot and cold running water and central heating. Victoria Mansion is open for tours from May through the first week of January, and 90% of the original interiors are intact.

Winslow Homer Studio

The famous Maine painter used this remodeled carriage house as his studio. Today it is owned by the Portland Museum of Art and tours are available departing from PMA. The tours must be booked in advance.

Maine State Building

A rare example of architecture from the Chicago’s World’s Fair, the Maine State Building was packed up in 16 boxcars and sent to Maine after the fair ended.

Parks in Portland Maine:

Eastern Promenade

This park stretches 68 acres along the waterfront and is home to East End Beach, a public beach. The park is home to free a summer concert series that takes place on Thursday nights in July and August.

Deering Oaks Park

Deering Oaks Park is home to the Saturday Farmer’s Market. And don’t miss the rose garden which is home to 600 rose plants and 38 varieties of roses.

Portland Maine Breweries:

There are 18 breweries in Portland alone!

Allagash

One of Maine’s most well-known breweries, Allagash offers a variety of tours and a tasting room. The tasting room has over a dozen beers on tap to taste.

Bissell Brothers

People are known to line up outside Bissell Brothers before the open just so they can buy some beer to bring home. The brewery is based on Thompson’s Point and they have a casual tasting room. Getting a pint is easy, it’s buying retail beer that is tricky because certain brews are released at very specific times and they usually sell out.

Rising Tide Brewery

This brewery’s tasting room is open 7 days a week and they offer public tours daily. They often host events and have food trucks on the premises.

Liquid Riot

Liquid Riot is part brewery, part distillery, and part restaurant located along the waterfront in the Old Port.

Oxbow

This farmhouse brewery produces ale and hosts a wide range of events including dance parties, fly tying classes, and yoga classes. The space doubles as an art gallery.

Shipyard Brewing Company

Maine’s largest brewery has a taproom in Portland. The brewery is famous for its Export Ale and Pumpkinhead.

Where to Shop in Portland:

Stonewall Kitchen

This brand that is known for its gourmet food products has a location in the Old Port.

The Old Port in Portland

The Old Port is one of the prettiest places in Portland. It has cobblestoned streets and is filled with locally owned boutiques and restaurants. Two of the main streets are Exchange Streets and Market Street.

Longfellow Books

An independent bookshop in the Old Port’s Monument Square that is known for promoting Maine authors.

Fitz & Bennett Home

Stocked with a mix of art, home decor, tableware, art, books, and beauty products, Fitz & Bennett Home is one of the best places to shop in Portland.

Folly 101

A beautiful shop selling a mix of homewares, kitchen goods, and gifts.

Portland Dry Goods

You can find big name and indie brands at this clothing store that outfits both men and women.

Bull Moose Music

The small chain of record stores has a shop in the Old Port.

Portland Architectural Salvage

“Everything old is new again” is the slogan at this giant store that helps to find a new home for salvaged items like claw foot bathtubs, doors, hardware, lighting, and house parts.

Blanche + Mimi

You can find a mix of interior design items, tableware, and antiques at this shop beside Stonewall Kitchen.

Salt Cellar

A shop that sells all things salt. From sea salts to salt lamps and beauty products, this place has a mix of salt themed goods.

Portland Trading Company

A shop selling men’s and women’s clothing, home goods, beauty products, and unique finds.

Cherished Possessions

Find second hand and vintage home goods and decor items at this store.

Music and Theater:

The Cross Arena (formerly the Civic Center) in Portland

One of the largest venues in Maine, The Cross Arena brings in a mix of concerts and other events.

Merrill Auditorium in Portland

Merrill Auditorium hosts touring Broadway shows, musical performances, the Portland Symphony Orchestra, and more.

State Theater in Portland

You can see touring musical acts like Cat Power, Dropkick Murphys, and Maggie Rogers here.

Portland Stage Company

This theatre company stages plays and musicals like A Christmas Carol, The Importance of Being Earnest, and The Last Five Years.

Mad Horse Theatre Company in South Portland

A theater that specializes in contemporary plays.

Where to Eat in Portland:

Eating and drinking are some of the best things to do in Portland, Maine. The city was doing farm to table before they had a name for it. I’ve listed James Beard Award winners along with locals’ favorites.

Central Provisions

Central Provisions brings creative and modern fine dining cuisine to a casual atmosphere. The menu changes daily, year-round, and they do not accept reservations.

Eventide Oyster Co.

A James Beard Award-Winning restaurant that specializes in oysters and seafood. The atmosphere is casual and fun and they serve traditional New England Clam Bakes.

Miyake

Chef Masa Miyake is a James Beard Award nominee and his namesake restaurant serves sushi, omakase, and meals created with ingredients sourced at the owner’s farm.

Otto Pizza

This pizzeria serves both single slices and full pies and is known for their creative pizzas like mashed potato, scallion, and bacon and butternut squash, ricotta, and cranberry.

Fore Street

James Beard Award-winning chef Sam Hayward serves up wood-fired cuisine at one of Maine’s best fine dining restaurants.

The Holy Donut

The Holy Doughnut makes their doughnuts with Maine’s largest agricultural product, potatoes. They make 16 flavors each day.

Standard Baking Co.

A family-owned bakery specializing in artisanal baked goods. They used Maine grown grains to make European style pastries like croissants, baguettes, scones, and madeleines.

DuckFat

A casual eatery that is a favorite among Portland locals and is known for serving Belgian duck fat fries and milkshakes.

DiMillo’s

DiMillo’s is a restaurant on a former ferry. It’s a little touristy, but it’s a classic. The menu focuses on seafood, and they also have kids and gluten-free menus.

Dutch’s

A casual cafe that serves diner style food with a Southern twist. In the morning they serve egg sandwiches on biscuits and at lunch, they serve a variety of sandwiches.

Hugo’s

A restaurant serving farm-to-table cuisine with global influences.

Honey Paw

A sister restaurant to Eventide Oyster Co. and Hugo’s serving Asian-fusion cuisine. Housemade noodle dishes like pork and crab mee goreng, a fried half chicken, and lobster wontons can be found on the menu.

Bao Bao Dumpling House

A dumpling house serving up creative dumplings with flavors like Kung Pao Chicken and Peanut, Bulgogi Beef, and Habanero Shrimp and Shiitake. It’s a great spot to stop for lunch.

Can’t-Miss Portland Bars:

Spend a night in Portland so that you can spend some time exploring the restaurant and bar scene. It’s worth it.

Mash Tun

Located next to Central Provisions, this low-key bar has a wide selection of local craft beers. It’s a nice early stop to make in Portland because it will give you a feel for which breweries you might like to visit.

The Great Lost Bear

A dive bar that my Dad loves, The Great Lost Bear has a large beer selection. Heads up, it’s outside of the Old Port and off a busy street, so you will likely need to uber to get there.

Novare Res

This bar in the Old Port has a large beer garden is known for having one of the largest beer lists in the state.

Hunt + Alpine Club

Portland might be a beer city, but cocktails are the thing to try at this bar/restaurant which is a two-time finalist for the James Beard Award for Outstanding Bar Program.

Lincoln’s

Named Lincoln’s because he is on the $5 bill and everything at this speakeasy is just $5. They don’t have a website or social media, and the place isn’t easy to find. To locate Lincoln’s, look for a pair of red double doors on Market Street between Milk Street and Fore Street. Enter through the red doors, go downstairs, find the bookcase and pull it to reveal the entrance to the bar. Don’t tell them I told you.

Cellardoor Winery

You will find Cellardoor Winery’s tasting room on Thompsons Point, beside the Cryptozoology museum and Bissell Brothers.

For a listing of happy hours and events in Portland, visit the Portland Old Port Blog.

Museums:

Portland Museum of Art

Right in downtown Portland, this is one of the best museums in the state. The museum features traveling exhibitions in addition to a permanent collection and is home to 18,000 works of art. There is an emphasis on artists who spent time in Maine.

Maine Historical Society and the Wadsworth-Longfellow House

The author of Paul Revere’s Ride, Henry Wadsworth Longfellow, grew up in this Portland home. Today the home is open for tours and it is filled with items owned by the Wadsworth and Longfellow families.

Children’s Museum & Theater of Maine

A children’s museum filled with activities and events for children and families.

International Cryptozoology Museum

A museum beside Bissell Brothers Brewing Company and Cellardoor Winery that is dedicated to mysterious animals like Bigfoot, the Loch Ness Monster, mermaids, yetis, and sea serpents. It’s the only museum of it’s kind.

Tate House Museum

Captain Tate was a Senior Mast Agent for the British Royal Navy stationed in Portland in the mid-1700s. The historic home has been turned into a museum and it is open from June to October.

Annual Events:

Valentine’s Day Bandit

One of the things that I love most about Portland is the Valentine’s Day Bandit. Each year Portland is mysteriously decorated with hearts. Some are small printouts, some are large banners on landmark buildings. The tradition started in 1976 and no one knows who is behind it.

Old Port Festival

A four-day family-friendly festival held in early June. The festival features a parade, live music, over 250 booths with food, crafts, art, and more.

Peaks to Portland Swim

An annual 2.4 mile open-water swim across Casco Bay from Peak’s Island to East End Beach. The event raises money for the YMCA of Southern Maine and takes place in July.