+ Dog Friendly Options too!
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In 2020, travel has had it’s limitations and restrictions. If you’re like me, you’re itching to get out and see something new, even if it’s just for the weekend. That’s why a 3 day weekend in Portland, Maine is a great getaway in the Northeast region of the United States.
3 days in Portland Maine is the perfect amount of time to get to see and do all the bucket list items. With its delicious food scene, classic New England architecture, lighthouses, and charming streets you’ll wonder why you didn’t plan a visit here before.
Is Portland, Maine Dog Friendly?
My dog Coco and I travel everywhere together. That’s why I’m always looking into pet-friendly destinations and Portland, Maine happened to be one of them. Not only is it a 1.5 hour plane ride from NYC, but the town, in general, is very dog friendly. Below you’ll find not only great itinerary ideas but also pet-friendly ones too.
Best Time To Visit Portland, Maine For a 3 Day Weekend
New England is beautiful all year long but the most popular time to go is Fall when the leaves start turning gold, orange, and red. I visited in October and although it was a little past peak season the colors were still beautiful. The weather was mid 50’s and very enjoyable. Although Fall, is my favorite time to visit New England why not visit in Spring or Summer. Below is an overview of the seasons.
- December-March: Winter in the Northeast can be EXTREME and it will make walking around the city not that enjoyable. However, if you’re planning on doing any winter sports upstate or in the surrounding area, Portland is a great stopover for some fantastic food and cheap hotel deals.
- April-May: Spring Because Portland is in the Northeast which means it could very well be snowing well into Springtime. Bring winter gear, boots, rains jackets, and thermal shirts. I recommend going in May, the weather should start warming up and you’ll only need a light spring jacket.
- June-August: Summer and High Season $$$ Like all cities, Summer brings crowds which means prices go up and availabilities for hotels and restaurants become harder to secure. Tourists flock to the nearby beaches, Acadia National Park, and of course Lobster Rolls.
- September-November: Fall Foliage Season! My personal favorite time to visit New England. Although Fall is high season the crisp Fall air and breathtaking colorful leaves make the crowds worth it. There are also plenty of day trips you can make into Maine to hike and see more Fall Foilage.
How To Get To Portland, Maine
Fly:
From NYC it’s about a 1.5-hour plane ride which makes a 3 day weekend in Portland, Maine such an easy getaway, especially with a dog. In the Northeast, you can usually find a direct flight for around $200 on a major airline. I use Skyscanner to always find the most convenient and cheapest flight deals. Fly into Portland International Jetport (PWM) from most major airlines. Once you land, it’s only a 15-minute car ride from downtown Portland.
Drive:
If you’re driving from NYC the ride is about 6 hours which is not ideal if you only have 3 days. However, if you have time and are traveling in the Fall, it’s a great chance to see Fall foliage.
Train:
For around $250 or less, you can take the Amtrak from several cities including Boston, New York, and DC.
Getting Around Portland, Maine
Spending a weekend in Portland, Maine is so easy if you don’t have a car. The city is really walkable for humans and dogs alike! There are also plenty of ubers and tours that will transport you to different locations. If you’re planning on visiting anything outside of town like Acadia National Park, then I recommend renting a car.
Best Area to Stay In Portland, Maine + Dog-Friendly Hotels
If you only have a 3 day weekend in Portland, Maine, then I recommend staying downtown to be close to everything. Check out my blog post on “How to Plan A Stress-Free Trip With Google Maps Trip Planner“, it’s a step by step guide on creating an entire itinerary in Google maps. By creating a well thought out itinerary you not only maximize your time on vacation but you save money too. Win-win!
Below are a few hotel options from budget to luxury and dg friendly too.
AC Hotel by Marriott Portland Downtown/Waterfront
Dog-friendly, airport shuttle, in the heart of downtown, walking distance to popular restaurants. $169/night
The Westin Portland Harborview
Dog-friendly, airport shuttle, in the heart of downtown, hotel restaurant, spa. $183/night
The Press Hotel, Marriott Autograph Collection
4 Star Hotel modern in the heart of downtown, airport shuttle, restaurant, rooftop. $230/night
Blind Tiger Guest House
4 Star Hotel in the heart of downtown classic with a modern twist, airport shuttle. $279/night
Things To Do In Downtown Portland For a 3 Day Weekend
Go On a Food Tour:
One of the best ways to discover a new destination is through the local cuisine, and Portland has no shortage of it. Book this food tour that includes a small intimate group of 14 people. The tour includes five food tastings and a locally guided small-group walking tour.
Walk Around The Old Port & Go Sailing:
The Old Port is a charming historic district with cobblestone streets and brick buildings by the port in downtown. It’s also full of small boutiques and the best seafood. Spend time walking around and admiring the ships in port, then go on a sailing tour!
Book this 2 hour Sailing tour for $48-$58 depending time of day. The company sails May-October. I recommend the sunset sail from 5-7pm.
Visit The Portland Museum of Art:
Home to pieces from the greats like Andy Warhol and Claude Monet, the Portland Museum of Art is a must-see on your trip to Portland, Maine. This unassuming museum is more of a boutique making it the perfect stop along your walk-in Old Port. Tickets are $18/adult and reservations are required for timed entry due to Coronavirus.
Day Trips From Portland, Maine For a 3 Day Weekend
Whether you’re planning a road trip to Maine, passing through Portland, or just spending a weekend, there are so many one-day road trips you can take from downtown. Below are 3 trips from Old Port that need to be on your 3-day weekend travel guide in Portland, Maine.
Head Light lighthouse (Dog Friendly)
One of the best-known landmarks of Portland is the famous Head Lighthouse. Located just 16 minutes from downtown Portland it’s easy to get there by car or uber and the whole area is dog friendly, best of all entry is FREE.
The park closes at sunset which is also the most popular time to visit. Tourists flock to the site to capture photos of the sun setting against the lighthouse. To avoid the crowds it’s recommended to come early in the morning.
Photo Tip:
To capture photos of the lighthouse-like the ones below, there are two points of entry.
- Front Facing Lighthouse: On the far right side of the park.
- Back Facing Lighthouse: On the left side of the park.
WARNING: There are rocks all around the lighthouse, so it’s a bit steep getting down into the areas where you’ll want to take photos, wear shoes with grip.
Acadia National Park (Dog Friendly)
Known as the Crown Jewel of the North Atlantic Coast, Acadia National Park is the perfect place to hike or just take in the views. The drive from downtown Portland is around 3 hours so plan on it being an all-day affair. The national park is dog friendly as well as has a beach for your fur baby to run around. Price is $30 per vehicle.
Allagash Brewing Company (Dog Friendly)
Portland is very well known for it’s buzzing beer scene. Check out the Allagash Brewing Company and try some local IPA’s. Located just 15 minutes north of downtown Portland. It’s also a dog-friendly brewery.
Where To Eat In Portland, Maine For a 3 Day Weekend
If you’re like me you want to try all the food there is to try when visiting a new destination. Portland has a fantastic food scene. Below are a the best restaurants in Portland, Maine to try.
DUCKFAT
A small family-owned restaurant serving some of the best not so light food in downtown Portland. The menu includes poutine with duck gravy, brisket sandwiches, and milkshakes. Highly recommend sharing as portions are large and not light bites. We had the cream of tomato fennel soup and shared the Poutine fires with a flight of sauces.
There are no reservations, seating is on a first-come basis and dinner crowds can wait up to 2 hours. To avoid a long wait time, go at lunchtime and wait only 45 min. Seating is all outdoors during COVID so feel free to bring your dog along.
CREAM OF TOMATO FENNEL 
POUTINE
Eaux
Soul and comfort food with a Northeast twist. Try the oysters with fried onions and the chicken & Waffles.
Cornbread with Apple Butter 
Oysters
The Highroller Lobster Co.
When you think of Maine you think of one food, lobster rolls! The Highroller Lobster Co. puts a twist on all their creations. Fresh baked brioche, Chopped Romaine, 4 oz of fresh Maine claw and knuckle meat, your choice of sauce. Build your own lobster roll and put whatever you want on it.
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Disclosure: Please note that some of the links above are affiliate links. I would never recommend anything I don’t personally love.
