Welcome to Portland!

A dog-friendly weekend in Portland, Maine! I’ve always loved Portland, it’s the perfect mix of coastal charm and creative energy. With its artsy vibes, welcoming locals, and an incredible food and beer scene, it’s a city I think everyone should visit at least once. But this trip was extra special—it was Leia’s first time exploring Portland, and I was blown away by just how dog-friendly the city really is.

From the moment we arrived, Leia was welcomed just about everywhere we went. It was rare that we ever heard, “sorry, service dogs only.” In fact, she spent only a couple of hours napping back at the Airbnb while we grabbed a quick drink or bite to eat. The rest of the time, she was living her best life, sniffing her way through the cobblestone streets of Old Port, making new friends, and joining us for adventures all over town.

We visited over Memorial Day weekend, which meant the city was buzzing with energy but not yet packed with the heavy summer crowds. It was the perfect balance of warm weather, ocean breezes, and plenty of space to explore without feeling rushed.

Now, let’s get to the good stuff - our favorite dog-friendly spots in Portland, Maine!

Where to Stay

Portland has no shortage of stylish, comfortable, and dog-welcoming places to stay. Whether you prefer a hotel with easy access to the waterfront or a cozy Airbnb with a little more space for your pup, there’s something for every traveler.

Our favorites:

• Aloft Portland – Modern, fun, and super pet-friendly. Dogs stay for free!

• The Westin Portland Harborview – Great views, spacious rooms, and a short walk to the Old Port.

• Canopy by Hilton Portland Waterfront – A trendy, central option where pups are treated like VIPs.

• Dog-friendly Airbnb – Perfect if you want a bit more privacy and space to relax between adventures

Where to Eat and Drink

If you’re a foodie or craft beer lover like me, you’ll feel right at home in Portland. So many spots have dog-friendly patios, making it easy to include your pup in your dining adventures. Here are a few highlights from our trip:

• Allagash Brewery – Iconic Maine beer and a super dog-welcoming outdoor space.

• Definitive Brewing – Great vibes, tasty brews, and friendly staff who were obsessed with Leia.

• Rising Tide Brewing – Spacious outdoor seating and a rotating lineup of local food trucks.

• Shipyard Brewing – A Portland classic and an easy stop if you’re exploring downtown.

• Independent Ice Co. – Cozy whiskey bar with a chill atmosphere.

• Papi – A lively Puerto Rican-inspired spot with incredible cocktails and small plates.

• Becky’s Diner – Classic, old-school breakfast by the water—don’t miss the blueberry pancakes!

• Island Lobster Co. – If you head out to Peaks Island, this is the place for lobster rolls and ocean views.

Note - many of the restaurants have seasonal patios, always check their website or social media for up-to-date policies

Where to Explore (Yes, it's all dog-friendly!)

Portland is packed with things to do, from city strolls to coastal adventures. Here are some of our favorite ways to explore with your pup:

• Wander through Old Port – Stroll the cobblestone streets, pop into local boutiques, and grab treats at Uncommon Paws, Fish & Bone, and Life is Good.

• Portland Discovery Land & Sea Tours – A fun way to see the city and harbor views (dogs are welcome on the outdoor decks!).

• Spend the day on Peaks Island – Take the Casco Bay Ferry, then rent a golf cart or bike to circle the island. Don’t forget to stop for lunch at Island Lobster Co.

• Walk the cliffs at Portland Head Light – One of Maine’s most iconic spots, perfect for photos and a breezy coastal stroll.

• Picnic at Two Lights State Park – Bring snacks (and a blanket) for a relaxing afternoon surrounded by ocean views.

Portland truly exceeded my expectations as a dog-friendly city. From breweries and restaurants to parks and ferries, Leia was welcomed everywhere with open arms (and plenty of ear scratches). It’s the kind of destination that makes traveling with your dog feel effortless and fun.

Whether you’re planning a weekend getaway or a longer New England road trip, Portland, Maine deserves a spot on your list. You’ll leave with a full heart, a full belly, and if your dog is anything like Leia, a very tired, very happy pup.