Home Food + DrinkBars A Weekend Getaway to Portland, Maine

A Weekend Getaway to Portland, Maine

by Samantha Impaglia
Attain Medspa
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Just a few hours from North Jersey and up the Northeast coast lies the state of Maine. Also known as Vacationland, there are so many towns to visit in this New England state. If you’re looking for a fun weekend trip, consider visiting Portland — a vibrant coastal town that lies on the southeast coast of Maine. From exploring Old Port to indulging in the local eats (including everything made with all the Maine blueberries we could find), we’ve rounded up all of the best things to do when spending a long weekend here. Read on for a guide to visiting Portland, Maine.

portland maine things to do

How to Get There

To get to Portland by car, it’s just over a five-hour drive from Hudson County. You can also fly into Portland International Jetport if you’re not a fan of long drives: flights from Newark Airport to Portland are about an hour and 20 minutes.

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Where to Stay


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We opted for an Airbnb during our stay in Portland since it was a cheaper option, but there are also a variety of hotels to stay in that are closer to Old Port and the downtown area. If looking for waterfront views of Portland Harbor, try AC Hotel by Marriott Portland Downtown/Waterfront, Canopy by Hilton Portland Waterfront, Courtyard by Marriott Portland Downtown/Waterfront, Hilton Garden Inn Portland Downtown Waterfront, Residence Inn by Marriott Portland Downtown/Waterfront, or The Press Hotel Autograph Collection. Other top-rated hotels in the area that are still close to everything include Portland Harbor Hotel, Portland Regency Hotel + Spa, The Docent’s Collection, The Westin Portland Harborview, and more.

Things to Do

Bayside Bowl | 58 Alder Street, Portland

Bayside Bowl is a unique spot that was one of our favorite stops on the trip. Downstairs is a bowling alley, and upstairs is a rooftop bar overlooking Portland. Bowling here costs $35 per lane per hour Monday through Thursday, $40 per lane per hour Friday through Sunday, shoe rentals cost $5, and socks also cost $5. There’s also a full food menu here, including items like smoked chicken wings, smash burgers, a cajun fried shrimp salad, crab cakes, and a variety of pizzas, among other dishes. Customers can visit the rooftop bar whether or not they decide to bowl — drink options include local beer, wine, and a rotating selection of featured cocktails. Food options include honey chipotle chicken tacos, burritos, a corn + bean bowl, zucchini tacos, chips with guacamole + salsa, and more. There’s also a rooftop film series going on here this summer, with movie screenings on select nights.

East End Beach | Eastern Promenade Trail, Portland

New England beaches may not be our beloved Jersey Shore, but they are still just as enjoyable. East End Beach in Portland is a beautiful, calm beach on Casco Bay with a view of the many islands off the coast. Hang out on the beach and enjoy watching the sailboats cruise around the bay or partake in some of the activities available here like swimming, rowing, kayaking, and boating.

Explore Old Port

portland old port

Old Port is full of breweries, restaurants, shops, and more to check out, and also offers pretty views of Portland Harbor. This is also where most of the hotels are located within Portland. For those with a sweet tooth, stop by the Old Port Candy Co. for a variety of treats. For plant lovers, Terrarium is an indoor plant shop and cafe where customers can make their own terrarium. Other shopping destinations include Bella Funk Boutique, Old Port Card Works, Uncommon Paws (for the pups), and more. For food and drinks, options include Gritty McDuff’s, Portland Lobster Company, Paper Tiger, and more. There are also several excursions and activities to try out in Old Port, including a Maine Brews Cruise, Wicked Walking Tours, and Rocky Bottom Tours, among others.

Portland Head Light | 12 Captain Strout Circle, Cape Elizabeth

This historical landmark is about 15 minutes south of Portland and is a must-visit when in the area. Take in the views of Cape Elizabeth and the Atlantic Ocean and explore the lighthouse, an award-winning museum that features lighthouse lenses and interpretative displays, and a gift shop. After visiting the lighthouse, head to the neighboring Fort Williams Park to find more ocean views, hiking trails, historical structures, sports and recreation areas, and more.

Places to Eat + Drink

Becky’s Diner | 390 Commercial Street, Portland

portland maine

Becky’s Diner is everything you can ask for when it comes to a typical diner: good coffee, good food, and classic diner vibes. This spot is located on Commercial Street near the water and serves up the normal diner fare for breakfast, lunch, and dinner 4AM-9PM daily (4AM-10PM during the summer). There are some specialty items on the menu, including a Commercial Street Sandwich with an English muffin, egg, cheese + a choice of ham, bacon, sausage, or tomato with home fries; a Fisherman’s Platter with fried Maine shrimp, haddock, scallops, + whole belly clams; and two locally caught one pound lobsters steamed and served with melted butter, among other dishes.

Bite Into Maine | Port Williams Park, Cape Elizabeth

After exploring Portland Head Light, stop by Bite Into Maine to try something that this state is known for: its lobster rolls. This food truck serves up a variety of fresh lobster rolls, sides, and drinks, all with a backdrop of Cape Elizabeth. Try out classic rolls like the Maine Style (with mayo + fresh chives), the CT Style (with warm butter), or the Picnic Style (with coleslaw, celery salt, + butter), or try something different like the wasabi or curry lobster rolls. Top it off with some potato salad and a Maine Root Soda and lunch is served.

Bubba’s Sulky Lounge | 92 Portland Street, Portland

Head outside the downtown/Old Port area a bit to experience a bar that will make you feel like you’re being transported back to the 1970s and 1980s. Bubba’s Sulky Lounge opened up on Portland Street in 1961 and is a truly one-of-a-kind experience in Portland. Upon walking in, customers are greeted with dark red lighting throughout and see the walls and ceilings lined with eclectic, vintage decor — from old movie posters and funky lamps to lunchboxes and mannequins. Seriously, there are so many interesting things to see in every corner of this bar. There are two dance floors at Bubba’s (one is lit up disco-style), so grab a drink at either of the two bars inside and dance to the throwback music.

The Holy Donut | 177 Commercial Street + 194 Park Avenue, Portland

holy donut portland

This doughnut shop has two locations within Portland (including two other Maine locations in Scarborough and Arunde) and specializes in potato doughnuts made from scratch daily. All of the flavors we tried here were delicious, and we definitely recommend one of the seasonal blueberry flavors — choose from blueberry glazed, blueberry cinnamon sugar, blueberry lemon, and Blueberry Holy Cannoli. Other flavors include honey lavender, maple, toasted coconut, fresh lemon, dark chocolate sea salt, and pomegranate. There are also several gluten-free versions of flavors, including fresh lemon, cinnamon sugar, vanilla glazed, dark chocolate sea salt, and old-fashioned.

Old Port Sea Grill + Raw Bar | 93 Commercial Street, Portland

Upon walking into this seafood-forward restaurant in Old Port, guests will first notice the 500-gallon saltwater fish tank behind the hostess stand. Old Port Sea Grill + Raw Bar features both a lounge area and a dining area and serves up local and imported fresh fish and shellfish, local craft beers, wine, and cocktails. The raw bar has options like oysters, clams, and chilled seafood, and some of the appetizers include New England Clam Chowder, tuna nachos, crab cakes, and more. The all-day menu also includes sandwiches and entrees — including lobster linguini, a smoked salmon BLT, grilled scallops + risotto, and fish + chips, among others. For those who prefer not to have seafood, there are options like fried Brussels sprouts, a black bean burger, classic bolognese, steak frites, and more.

Rigby Yard | 50 Wharf Street, Portland

Situated on the cobblestone alley that is Wharf Street, Rigby Yard is a homage to the Rigby Yard Train Depot — which served as a link to all of the North East for many decades, per the website. The restaurant serves up New England-style eats, with options spanning from whipped ricotta and buffalo cauliflower to pan-seared halibut and a Southern fried chicken sandwich. HG pro tip: Try the BBQ Pulled Port Sliders, pictured above. Dessert dishes include the Rigby Bread Pudding, fried ice cream, and more. For drinks, there is Maine craft beer on tap, wine, and champagne, as well as specialty cocktails including a Knight Train Espresso Martini, peach bourbon lemonade, Cherry Smash, a pomegranate Cosmo on tap, and more.

The Porthole Restaurant + Pub | 20 Custom House Wharf, Portland

the porthole

The Porthole opened up in 1929 as an early breakfast spot for lobster fishermen, and today it continues to serve the working waterfront and support local aquaculture by serving top-quality, local seafood. The spot provides amazing views of Portland Harbor, and you can have a drink out on the deck or sit down inside and get something to eat. Breakfast, lunch, and dinner are served here — menu highlights include Haagen-Das French Toast, a raw bar, Bang Bang Shrimp, lobster spring rolls, fish tacos, a blackened haddock sandwich, baked stuffed lobster, a clambake for the table, and more. There is also live music almost every night at The Porthole.

ViA VECCHiA | 10 Dana Street, Portland

ViA VECCHiA is an upscale, Italian-inspired restaurant located in the heart of Old Port that serves up a combination of old-world Italy and coastal Maine dishes — possibly our favorite restaurant of the trip. The exterior of the building is covered in vines, and the inside boasts a warm and comforting vibe complete with dim lighting and velvet booths. Customers can also dine on the outdoor patio in the front of the building. The restaurant has an extensive drinks menu, complete with cocktails like a Sicilian Negroni (gin, Campari, Amaro Dell’Etna, + Salted Grapefruit Oleo); Hey Mambo! (tequila, mezcal, Luxardo aperitivo, coconut, pineapple, + lime, blended); and a Florentina Spritz (San Bitter, grapefruit, lemon, + soda), among others. HG pro tip: Start off your meal with the sourdough bread + house butters as well as the burrata. For entrees, choose from pizza, pasta, and large plates like ravioli with garlic ricotta, Maine lobster, corn, tomato fonduta, fresh basil, + stracciatella cheese; a Central St. pizza with Italian sausage, pickled hot pepper, mozzarella, + whipped ricotta; a pan-seared 6-ounce filet with gnocchi, balsamic pearl onions, red pepper fonduta, + piave frico; and more.

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Wilson County Barbecue | 82 Hanover Street Suite 8, Portland

This barbecue spot is located outside the downtown/Old Port area a bit, but worth the short trek. Using recipes and techniques handed down through generations of the Brantley family of Wilson County, North Carolina (hence the name), customers can find traditional Eastern North Carolina, pit-smoked whole hog-style barbecue here. The inside sports a full bar complete with TVs, and there’s both indoor and outdoor seating. We chose to come here for a nightcap, and the string lights and red glow of the sign created the perfect atmosphere for a drink outdoors — choose from a strawberry mint margarita, a white peach mojito, and more. On the menu, there is an array of barbecue dishes including baby back ribs, barbecue chicken, a fried shrimp po’boy, a pimento cheese biscuit, hushpuppies, and pork belly burnt ends, among others. Wilson County Barbecue also serves brunch on Saturdays and Sundays from 9AM-3PM, with dishes like chicken + waffles, pork belly benedict, and more.

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