What to do in Portland, Maine while house and pet sitting

Find yourself pet sitting and wondering what to do in Portland, Maine? With its scenic coastline and quaint coastal buildings, Portland, Maine is New England’s dog-friendly paradise. Maine’s largest city has so much to offer and combines small-town charm with incredible scenery, great breweries and pet-friendly beaches.  

Read on to discover all the things you can do in Portland, Maine and our top picks to have the best time while you’re looking after your latest sit. 

Portland, Maine attractions

When it comes to what to do in Portland, Maine, there’s an eclectic mixture of artistic and outdoor adventures to choose from. From lighthouses, great beaches and of course fresh lobster, the stylish spot means you really are spoilt for choice.

1. Casco Bay Islands

At Casco Bay there’s an island for every day of the year. Actually, there’s approximately 785 islands and exposed ledges in the Bay altogether. Discover the largest island Chebeague at almost 5 miles long with many spectacular buildings like the Washington Monument. 

2. Portland Museum of Art

Head to Downtown Maine when you’re looking for some culture. The Portland Museum of Art, or PMA, is the largest and oldest public art institution in Maine. The museum has an extensive collection of exhibitions including American, European and contemporary art, as well as works celebrating the diverse artistic traditions of Maine. 

3. Victoria Mansion

A much-loved Portland landmark, Victoria Mansion is regarded for its architecture and extraordinary interiors. As one of the most important historic homes of the 19th century, the Victoria Mansion is a must-see. Do a tour or go to one of the many seasonal events. 

4. Portland Head Light 

Located in Cape Elizabeth, the Portland Head Light is the oldest lighthouse in Maine and has some of the best coastal views around. The light station is automated and the tower, beacon and foghorn are maintained by the US Coast Guard. Can’t resist a museum? Visit the former lighthouse keepers’ house, transformed into a maritime museum.

5. Maine Narrow Gauge Railroad

If you’re a railway enthusiast (or not!) the Maine Narrow Gauge Railroad Co. & Museum is a must-visit. Consisting of passenger and freight equipment, as well as artifacts from the 2 ft narrow gauge railways that ran in the state of Maine in the late 19th century and early 20th century. 

Free things to do in Portland Maine

1. Old Port

The Old Port is a quaint historic district with cobblestone streets and brick buildings with a wide variety of boutiques, gourmet food stores and souvenir shops. If you’re looking for a night time spot, there’s pubs, breweries and cocktail bars as well as plenty of restaurants to choose from.

2. Harbor Fish Market 

It’s hard to resist the ocean air when you’re exploring the Old Port. If you’re a fan of seafood, your go-to destination is the Harbor Fish Market. Here you’ll find more fresh seafood than you could possibly ever want, including lobster and haddock to rare finds like dorado. 

3. Eastern Promenade

Looking for somewhere to take your pup when you visit? The 2-mile Eastern Promenade Trail is one of Portland’s best harbor-side walks. The Eastern Promenade is dog friendly too, with an off leash area next to Fort Allen Park and East End Beach. 

4. Cape Elizabeth

Cape Elizabeth is home to scenic Fort Williams State Park, the picturesque Portland Head Light and miles of beaches and coastal waterfront.

5. Portland Public Library

Aside from an incredible library, Portland's city library also offers so much more. On any given day of the week, there are free talks by renowned authors, readings by book groups, documentary film screenings and art exhibits.

Fun things to do in Portland Maine

1. Commercial Street 

The historic street is situated at the edge of the working waterfront area of Portland. Here you can discover unique pottery and souvenir shops, quaint restaurants and nice trails for walking.

2. Brewery Tours

Hop on a brewery tour if you’re after the ultimate tasting session. There’s lots of all-inclusive tours and experiences that give you a behind-the-scenes look at Maine's craft breweries, distilleries, wineries and more.

3. Portland Observatory

The Portland Observatory is a historic maritime signal tower at 138 Congress Street in the Munjoy Hill section of the state. Built in 1807, the must-see observatory is the only known surviving tower of its type located in the US. 

4. Spring Point Ledge Lighthouse 

If you’re looking for an activity that really screams Portland, be sure to visit the Spring Point Ledge Lighthouse. The historic lighthouse is situated at the end of a 900-foot breakwater wall that borders the Atlantic Ocean. Take a short walk along the breakwater wall or visit during an open house, a tour done by Trust volunteers. 

5. Portland’s Free Concerts 

Celebrate global music at one of Portland’s free concerts. From spring to early fall, free concerts are put on during noontime, after-work and during the evening, all throughout the city. It’s a great way to discover new music for no charge. 

What to do in Portland, Maine with pets?

Looking for things to do in Portland, Maine with your latest pet sit? Pet-friendly Portland is a hub of activity for you and your pooch. Here’s just a few of our favorite things: 

1. Visit a brewery 

Portland has almost 20 dog-friendly breweries to visit with your pup. Head over to the Old Port to sample small-batch ales and pub grub at Gritty McDuff’s Brew Pub (aka Gritty’s) or The Thirsty Pig, a cool hangout which serves craft beers and house-made sausages. Dogs are welcome to join you for a nightcap at both places.

2. Standard Baking Co

A visit to Portland isn’t complete without visiting Standard Baking Co. You can sit with your pup at one of the outdoor tables located directly across from Portland’s harbor while enjoying a coffee and a hand-rolled croissant. What could be better?

3. The East End Beach 

Visiting during the summer months? The East End Beach at Eastern Beach Promenade Park offers off-leash play for dogs in the summer before 9 a.m. If you're sitting a pup that adores the water, there’s Willard Beach in South Portland, which allows dogs to swim in the water from 7 a.m. until 9 a.m.

4. Beals Famous Old Fashioned Ice Cream 

Treat both of you to a sweet treat at the end of a busy day. Your fur-friend can enjoy a dog-friendly scoop of ice cream while you sit at a picnic table on the picturesque cobblestone street.

Best restaurants in Portland, Maine

Wondering what the best restaurants in Portland, Maine are? From 5 star diners to amazing seafood restaurants, there’s no shortage of delicious fare in Portland: 

1. Solo Italiano 

With an impressive menu that changes daily, Solo Italiano is a must-visit if you love Italian cuisine. Enjoy delicious handkerchief pasta, rolled thin and smothered in homemade sauces. The wine list’s not too shabby, either.  

2. Central provisions 

For something different, try Central Provisions. Chef Chris Gould organizes small plates into simple designations: raw, cold, hot and sweet. You get to mix and match a few dishes from each or stick with a dominant flavour. We recommend Gould's signature suckling pig and French fries seasoned with Korean-chili spice.

3. Rose Foods 

Looking for a great lunch spot? Rose foods specialize in sourdough bagels that take 3 days to make to completion. Choose from six flavors daily: five classics and one rotating special. It could be a classic like egg, or an inspired flavour of Sichuan chili, herby ranch, or chili-garlic-fennel. Take a couple home to enjoy the following day.

4. Scales 

A trip to Portland wouldn’t be complete without indulging in some seafood. One of the best seafood restaurants in Portland, Maine is Scales. Set in a post-industrial warehouse in Portland’s Old Port neighbourhood, the restaurant specialises in freshly caught whole fish, including octopus, oysters and clams. Make sure you reserve a table cause it’s a busy one.

5. Chaval 

When only tapas will do, take a visit to Chaval. There you’ll find classics like patatas bravas, deviled eggs, queen olives and local wild mushrooms. Save some room for a sweet as there’s indulgent chocolate pudding with smoky serrano ice cream on offer.

With so many exciting attractions to enjoy in Portland, we’re sure you’ll get the travel bug and want to explore more and more places as you pet sit. So, why not look for another pet sitting assignment? Remember, there is no limit to the amount of pet sits you can do and you can travel as far afield as you’re prepared to. And don't forget to share your pet sitting adventures with us on Facebook and Instagram, and share your experiences on our Community Forum!