Portland, Maine is a gorgeous city of adventure set on exploring beautiful scenery and character. The diversity behind the city alone proves that it is a great spot to visit any time of the year. It just so happens that taking a nice road trip to the gorgeous peninsula will pay off extremely well. Imagine having the top down in your car during the soothing summer days, driving through the town while stopping off at some incredible attractions. All it takes is one weekend set aside for yourself to come and experience the magic that Portland, Maine has to offer! All you would have to do is follow this guide that is made specifically for this piece of heaven. Let’s get started.


It is good to know that no matter the time of year that you choose to visit Portland, they will accommodate accordingly. The winters are packed with winter retreats and weekend getaways. Whether you like skiing or snowboarding, they will take care of you. As for summer, you will be able to roam freely along the water with more comfort. July and August are generally the most visiting times. Overall, it is fantastic that this place is awesome year-round. 

Old Port

People tend to gravitate to the working waterfront when they are in Portland, Maine. Here, the boats come and go into the waters and you can walk around and socialize in their sophisticated urban center. Even if you are keeping to yourself, this portion of the trip will have you in awe. Walk on through to Old Port, where the streets are made of cobblestone, and the lobster is one in a million. Old Port makes for a great evening of dining and dancing. Even if one is just into shopping around, they will find many great boutiques here. Who knows, you might even meet someone that will take you on a gorgeous, sunset boat ride. Old Port is highly recommended to visit if you are staring off your trip. It is a great way to get a taste of what Portland is all about. 

Cape Elizabeth

This is one of those places that you have seen hundreds of times but have never been there. It is probably because Cape Elizabeth’s Portland Headlight is one of the most photographed lighthouses in the world. It is such a gorgeous place to view the sunrise and sunset that people who have lived there their whole lives still watch is religiously. The lighthouse was commissioned in the late 1700’s by none other than George Washington. How neat is that? Next, you can head on over to the 94-acre Fort Williams Park. You will stumble upon old ruins such as the Goddard Mansion. Some of the forts here helped house troops in World War I and World War II. As you can see, Cape Elizabeth is a hot spot for learning about the history of Portland, Maine. 


Located just outside of Portland, Scarborough is one of those rare towns where you cannot stop running into scenes that look like they are straight out of a movie. Don’t believe me? Just take a gander at the Rachel Carson National Wildlife Refuge. This is a large salt marsh that paints its way through the distance. When you go, you can hike the trails and go bird watching. For another amazing sunset, taking a trip over to Prout’s neck will prove to be worth your time. Sometimes, people get tired of looking and want to hop into the scenery themselves. Scarborough Beach State Park will allow you to do just that. Loaded with fun, water, and lifeguards, you will be good to dive right in at your convenience. 

Portland, Maine is filled with many more opportunities for your weekend travels. So much so, that your weekend getaway might turn into a full-blown week! There are also wonderful hotels and places to stay while you are there. If you can swing it, you might want to check out the Michelin star restaurants located near the waterfront. This will be some of the best seafood you ever experience. Regardless, Portland will make for a fantastic trip that will have you wanting to come back for more. Please drive safe, and have tons of fun on your weekend getaway!

Blog post courtesy of Clay Pitsenbarger, freelance journalist who loves the New England Patriots and Country Music.