Getting to Portland
Portland, Maine is about two hours north of Boston. It makes a fine road trip, but once you hear all the options, you’ll be want to book a long weekend.
Your trip starts as soon as you cross the state line. Once I’m in Maine, the air somehow smells fresher. Maybe it’s just the relief of surviving the I-95 in Massachusetts, where the speed limit is a mere suggestion. But take a deep breath. The smell of pine mingling with ocean air will tell you you’ve left the big city.
Maine is synonymous with lobster. If you stop at any small town along the coast, you’ll find the savory state specialty on offer. In Kittery, grab a bite at Bob’s Clam Hut. If you want to try something other than lobster, I’m always partial to the fried whole clam bellies, clam strips, or the fried scallops.
On the drive from Kittery to Portland, there are several opportunities to experience coastal Maine. York, Ogunquit, Kennebunkport, and Old Orchard Beach are all scenic places to make a pit stop and walk around. York, Ogunquit, and Old Orchard all have beautiful sandy beaches.
York is home to the most photographed lighthouse in Maine, Nubble Light on Cape Neddick.
Kennebunkport is best known today as the summer vacation spot of the President George H. W. Bush and his family. You can get a good look at the compound if you take a spin on Ocean Drive. The homes sit on Walker’s Point and there’s a place to pull over near the compound. It’s easy to see why the family loves the area. The town of Kennebunkport is quaint, with lovely shops and restaurants, and the views are spectacular. If you want to extend your stay, take a guided kayak tour, or see how that lobster really makes it onto your plate during a ride on a lobster boat.
To experience any of these towns, you can wind your way through them on your way to Portland, or pick one or two and just jump off the I-95. It’s less than an hour if you take the interstate straight from Kittery to Portland. Taking the scenic route could set you back three-plus hours depending on how often you decide to stop and whether you’re visiting during the busy summer and fall months.
Beers for fears
Portland is known for its excellent craft brew scene. It’s more than just hitting a brewery here or there; there’s an area of Portland that’s home to several breweries, all within 100 yards of each other.
Allagash Brewing Company consistently tops any ‘best craft breweries’ list in New England; not just Maine, the entire six-state area. It can take up to 45 minutes to get here from downtown Portland with traffic, but it’s worth it. This place won my heart on our first visit several years ago. When my husband and I walked in with our 3-year-old twin boys, the first words the staff said to us were, “Could we get them a juice box and a snack?” Sold! I will come here until the day I die, or until the doctor tells me I must stop drinking beer.
But Allagash’s beer is the real star. You can either sample in the tasting room for a few bucks, or reserve the Grand Cru Tour. It’s a three-hour experience with barrel-tastings, a look at the bottling line, and chats with the folks who make it all happen. It’s $100 per person, but 100% of the cost goes to charity. Also, there could be a wait for the tasting room, especially during the popular summer months, so get there when it opens.
Another perk about being at Allagash: eating a lobster roll from one of Portland’s best food trucks. Bite into Maine is known for the New England specialty, which you can get either Maine style (cold with mayo) or Connecticut style (hot with butter). You can also try a Lobster Grilled Cheese or the Triple B (bacon, brie and local blueberry jam on butter grilled sourdough bread). The food truck is open seasonally.
Across the street, there’s an industrial warehouse which has been home to several brewery start-ups since 2009. Today it’s home to Austin Street Brewery, Battery Steele Brewing, and Foundation Brewing Company. These breweries do have tasting hours as well if you are into the craft beer scene. If not, you’ll score major cool points just for knowing this little corner of beer heaven exists.
What to do downtown
Downtown Portland is an interesting collection of quirky storefronts, tantalizing food, art galleries, historic homes, and a working waterfront. Old Port is the revitalized warehouse district. It’s an easy one-stop shop for tourists and locals, with cobblestone streets and plenty of restaurants.
Portland also fosters a thriving art scene. Its Museum of Art displays works by Renoir, Monet, and Warhol, but it also highlights works by Maine artists. The museum does charge admission, but it is free on Fridays from 4-8 PM.
The museum also gives visitors the opportunity to tour artist Winslow Homer’s studio. The 2 ½ hour tour leaves from the museum and allows you to see the area that inspired his work. You must reserve your spot in advance. The $55-$65 admission for the studio tour includes admission to the Museum.
In addition to the Portland Museum of Art, the art community hosts First Friday Art Walks throughout the year. You can browse the shops, watch live performances, and buy work from street artists. It’s the perfect time to find the perfect piece to remember your visit.
Make a splash
It’s hard not to want to be on the water when you’re in Portland and there are a variety of ways to do it. Nothing gets you closer to the water, literally, than a kayak. Portland Paddle offers a variety of guided tours starting at around $40 per person. They offer sunset and moonlight tours, as well as half and full day excursions.
Another option: take the Casco Bay Lines ferry to Peaks Island and rent your kayak at Maine Island Kayak. Renting here allows you to explore the outer islands of Casco Bay. It’s not only about rocky shores. From wildlife, to a fort, to a shipwreck, it’s an adventurous way to experience Maine. Tours start at $70 per person.
Depending on the length of your tour, you can also rent bikes or a golf cart to take in the rest of scenic Peaks Island. One tip: food choices are limited on the island. It may be worth bringing over your own lunch or snacks for your visit.
Another option to get out onto the water is to see how Maine lobstermen make their living by booking a cruise with Lucky Catch. It’s about a 90-minute excursion and you’ll come away with an entirely new vocabulary to impress your friends with: hard shells, shedders, shorts, culls, and keepers.
If two of your favorite W words are wine and water, check out Wine Wise. If you didn’t pick up on the hint from the company’s name, this isn’t just a sip and drift into la-la land type of Casco Bay cruise. Sommelier Erica Archer is going to teach you about what you’re drinking while you enjoy views of lighthouses and the islands. You’ll also learn about wine/food pairings and how to properly describe a wine’s smell and taste. The sail costs around $150 per couple.
If you prefer to stay on dry land, you can pick one of Summer Feet Cycling’s bike tours. This is not the Tour De France, but you will be cycling anywhere from 4 to 30 miles depending on which tour you choose. If you can handle a 12-mile ride, try the 5 Lighthouse Tour. You’ll peddle along the shores of Casco Bay and, as the name suggests, see five of the area lighthouses. It lasts from four to five hours. Bike, guide, and lobster roll are included for about $100 per person. Reservations are recommended.
Just north of Portland, Freeport is home to well-known outdoor clothing and equipment company, L.L. Bean. Its Outdoor Discovery School offers instruction on everything from photography to fly fishing. Course lengths range from about an hour to a full weekend.
Food and culture
There is plenty of history in Portland. One stop is the Wadsworth-Longfellow House. Built in 1785, it was the childhood home of poet Henry Wadsworth Longfellow. Practically all the furniture is original to the Wadsworth Longfellow family.
Also, check out Victoria Mansion. It’s one of the most fascinating extant nineteenth century homes anywhere in the country. Its asymmetrical design is so unusual and rare that it was declared a National Historic Landmark in 1971.
A trip to Portland is not only visually pleasing, but also palate pleasing. The city has a fantastic food scene and is home to several James Beard Award recognized chefs.
The restaurant Fore Street started it all. It was locally sourced before locally sourced was cool, and it’s credited with catapulting Portland onto the world stage. Chef-partner Sam Hayward was named “Best Chef-Northeast” by the James Beard Foundation in 2004. The Old Port restaurant has also been James Beard nominated for “Outstanding Restaurant” three times. They do take reservations, but they also hold a third of their tables for walk-ins. Just be sure to get there by 5 PM when they start taking names for those seats.
The line out the door at Central Provisions an hour before dinner should tell you that it does not accept reservations. The young restaurant was a James Beard Award nominee for Best New Restaurant in 2015. Owner/Chef Christopher Gould and his wife, Paige, pride themselves on supporting local farmers and craftsmen. From the seats to the bar to the bathroom door, everything was made locally. One tip: They do keep lunch hours most days of the week, and it’s easier to snag a table starting at 11 a.m.
Two more restaurants to try with James Beard attached to their resume: Duckfat, and Eventide Oyster Company. From their names, you can guess these restaurants have a different focus than those above. But if you’re in the mood for poutine or oysters try one of these Portland gems.
If you’re now convinced your trip to Portland needs to be an overnight stay, try the Pomegranate Inn. Foodie Alert! The breakfast at this charming inn makes it worth booking a stay.
Portland Harbor Hotel is another place to rest your head. It’s in the Old Port area and offers complimentary bikes for a ride around town – after you’ve enjoyed your complimentary Starbucks coffee, of course!