The Ultimate Weekend Guide to Portland, Maine’s Old Port
Portland, Maine’s Old Port is a charming place for a weekend getaway. With cobblestone streets, historic brick buildings, waterfront views, local shops, breweries, and plenty of restaurants, the area has a little bit of everything.
The best part is that you can explore much of the Old Port on foot. Spend your days walking around downtown, trying local food, browsing shops, and enjoying the waterfront. You can also take a short drive outside the area to see one of Maine’s most famous lighthouses.
If you are planning a weekend in Portland, Maine, here is everything you need to know about staying and exploring the Old Port.
You may also like to read this: 30+ Best Things to Do Alone in Los Angeles: Solo Travel Guide
How to Spend a Weekend in Portland, Maine’s Old Port
Getting There
If you live within driving distance of Portland, driving is one of the easiest ways to get there. If you are coming from farther away, you can fly into Portland International Jetport.
The airport is only a short drive from the Old Port, making it easy to get to your hotel after landing. Once you arrive in the Old Port, you can leave the car parked and explore much of the area on foot.
Where to Stay in the Old Port
Staying in or near the Old Port makes a weekend trip much easier. Many restaurants, shops, bars, and attractions are within walking distance, so you do not have to spend much time driving around.
The Portland Harbor Hotel is one option in the heart of the Old Port. It offers comfortable rooms and puts you close to many of the area’s main attractions.
Another option is the AC Hotel by Marriott Portland Downtown/Waterfront. It is within walking distance of the Old Port and is a convenient choice if you want to stay near the waterfront.
The Press Hotel is another option in the area. Its historic setting and central location make it a convenient base for exploring Portland.
Do You Need a Rental Car?
You can easily spend a weekend in the Old Port without a rental car. Walking is one of the best ways to explore the neighborhood, and rideshare services are available when you need a ride.
A car becomes more useful if you want to explore places outside downtown Portland. For example, Portland Head Light is a short drive from the Old Port.
If your plans are mostly focused on downtown, you can avoid the hassle of parking and skip the rental car.
Best Things to Do in the Old Port
The Old Port is easy to explore at a relaxed pace. You can spend the morning walking along the waterfront, stop for lunch, browse local shops in the afternoon, and enjoy dinner and drinks in the evening.
Here are some of the best things to add to your weekend itinerary.
Walk Around Downtown
One of the simplest ways to enjoy the Old Port is to walk around and take in the atmosphere.
The neighborhood is known for its cobblestone streets, old brick buildings, local businesses, and waterfront setting. Take your time exploring the streets instead of rushing from one attraction to another.
You will also find plenty of places to stop for coffee, food, or a drink along the way.
Go Shopping
The Old Port has a mix of familiar brands, independent stores, boutiques, and local shops.
You can browse clothing, gifts, home goods, souvenirs, and other locally made items. Even if you are not planning to buy anything, walking through the shopping district is a fun way to spend an afternoon.
Explore Portland’s Breweries
Portland is well known for its craft beer scene, and a visit to the city gives you plenty of opportunities to try local brews.
Some breweries are close to the Old Port, while others require a short drive or rideshare trip. Breweries to look into include Bissell Brothers, Allagash, Oxbow, Banded Brewing, Liquid Riot, Rising Tide, Shipyard, and Definitive Brewing.
If you plan to visit several breweries, use a rideshare service rather than driving yourself.
Visit Portland Head Light
Portland Head Light is one of the most popular places to visit near Portland. The historic lighthouse sits along the rocky Maine coast and offers beautiful ocean views.
You can walk along the surrounding trails, take photos, and spend some time enjoying the coastal scenery.
It is only a short drive from the Old Port, making it an easy addition to your weekend plans.
Where to Eat in the Old Port
Food is a big part of the Portland experience. The Old Port has everything from casual breakfast spots and pizza to seafood, tacos, and nicer restaurants.
If there is a particular restaurant you really want to try, making a reservation ahead of time is a good idea, especially for a weekend visit.
Best Places for Breakfast
Becky’s Diner is a classic choice for a traditional breakfast. The menu is large, and it can get busy, so arriving early can help you avoid a long wait.
The Crooked Mile Cafe is a convenient option if you want something quick. Grab a breakfast sandwich or burrito before heading out to explore.
The Holy Donut is worth a stop if you want to try something different. The shop is known for its potato donuts, a popular Maine treat.
Read more: Christmas in Charleston, South Carolina: A Magical Holiday Experience
Best Places for Lunch
El Rayo Taqueria is a good choice when you are craving tacos and Mexican food.
Portland Pie Co. is a casual option for pizza, with a variety of pies and drinks to choose from.
Bite Into Maine is a great option for trying a classic Maine lobster roll. Depending on the location and season, you may find the food truck near popular attractions such as Portland Head Light.
Taco Escobarr offers tacos, burritos, and margaritas in a lively setting.
For something a little different, stop at Micucci Grocery. This Italian grocery store is known for its famous slab-style pizza. One slab is plenty to share, so keep that in mind when ordering.
Best Places for Dinner
For a special dinner, UNION Restaurant at The Press Hotel offers a menu focused on local ingredients. It is a good choice for a more polished meal during your weekend.
ViA VECCHiA is another option if Italian food is on your list. Its location in the Old Port makes it easy to reach after a day of exploring.
For a more casual Portland experience, try Duckfat, a well-known local spot famous for its fries and other comfort food.
Reservations are recommended for popular dinner spots, particularly on Friday and Saturday nights.
Enjoy the Old Port Nightlife
The Old Port does not shut down when dinner is over. There are plenty of bars and pubs where you can continue your evening.
Bonfire Country Bar has a country-themed atmosphere and a lively late-night setting.
Fore Play Sports Pub is another casual option if you want to watch sports and enjoy drinks.
You can also stop by Bull Feeney’s, a popular Irish-style pub in the Old Port.
Whether you want a lively bar or a more relaxed place for a drink, you will find several options within walking distance of the main downtown area.
Why Visit the Old Port in Fall?
Fall is a beautiful time to visit Portland, Maine. The weather can be comfortable for walking during the day, while evenings bring cooler temperatures and a cozy atmosphere.
Fall can also offer a quieter feel than the busiest summer weekends. You can spend the day walking the cobblestone streets, exploring shops, visiting breweries, and taking a trip to Portland Head Light.
October is especially appealing if you want to experience New England fall scenery while exploring the coast.
Conclusion
Portland, Maine’s Old Port is an easy destination for a weekend trip. You can stay close to the action, walk between many of the area’s restaurants and shops, and still have time to explore attractions outside downtown.
From seafood and local breweries to cobblestone streets and coastal views, there is plenty to keep you busy for two or three days.
If you are looking for a simple New England getaway, Portland’s Old Port is worth adding to your Maine travel plans.
Frequently Asked Questions About Portland, Maine’s Old Port
Is Portland, Maine’s Old Port worth visiting?
Yes. The Old Port is a great place to explore Portland’s historic streets, waterfront, restaurants, shops, breweries, and nearby attractions.
How many days do you need in Portland’s Old Port?
A weekend is enough to see the main sights in the Old Port, enjoy several restaurants, and take a short trip to places like Portland Head Light.
Can you walk around Portland’s Old Port?
Yes. The Old Port is very walkable, and many shops, restaurants, bars, and waterfront areas are close together.
Do you need a car in Portland, Maine?
You do not need a car if you plan to stay mostly in the Old Port. Walking and rideshare services can get you around, but a car is useful for exploring areas outside downtown.
What is the best time to visit Portland’s Old Port?
Fall is a popular time to visit because of the comfortable weather and beautiful New England scenery. Summer is also a good choice if you prefer warmer weather and more activity.
