SharpRomance Destinations: A Taste of Portland, Maine

Submitted by SharpMan Editorial Team on Tuesday 12th October 2010
In this article
  • Spectacular views and autumn colors.
  • Where to buy cool stuff.
  • Where to eat.
SharpRomance Destinations: A Taste of Portland, Maine

During the July 4th fireworks celebration of 1866, a young boy unknowingly started a fire, destroying more than half of Portland, Maine before the fire was extinguished. Today cobblestones weave a path past galleries, coffeehouses, antique shops, and restaurants, all housed in historic buildings. Welcome to the heart of the Old Port, Portland, Maine, a small city resting on the edge of a working harbor. If you’re looking for a low-key romance destination, consider this SharpRomance gem:

Why Portland, Maine? Sharp Views and Nature Spots

Despite all the local charm, the greatest reason to bring your SharpWoman to Portland is the view of the coast. When the sunlight begins to ebb and the water turns a fire-red, you’ll find yourselves in the most romantic of settings. In fact, from the West End to the East End of town, you’ll find a number of beautiful spots from which to bask in warm light of a sunrise or watch the vibrant colors of the sunset.

For spectacular views, head over the Million Dollar Bridge into South Portland: stay straight on Broadway and follow the signs for Spring Point Museum. If you get lost, just ask any local. The view will be worth it.

Another beautiful sight is Portland Head Light, the first established beacon light upon the New England coast. Lighted for the first time January 10, 1791, Portland Head sits high above the vast Atlantic sea providing spectators with panoramic views that stretch for miles. Just beyond the shops and restaurants lies Portland's only waterfall, Jewel Falls, on the grounds of the Fore River Sanctuary, (207) 781-2330. This 76-acre preserve owned by the Maine Audubon Society offers 2 1/2 miles of hiking trails.

Another unique place rests on the East End of the city: 102 steps to the top and you'll be looking out from the last surviving 19th-century signal tower, the Portland Observatory (138 Congress Street (207) 772-5561). The tower offers panoramic views of the city and Atlantic Ocean.

Autumn Leaves

Most people come to Maine in the fall in order to view the changing leaves. This is the time of year when the greenest of trees fade into warm autumn colors. So pack a lunch, bring a sweater and take your SharpWoman for a walk down to Deering Oaks. This 51-acre city park features a beautiful pond full of ducks and swans, fountains, paddleboats and a towering grove of oak trees — perfect for Sharp-style romance.

Every Saturday morning throughout the summer and into November you’ll also find a farmer’s market offering fresh cut flowers and a variety of Maine produce, including pumpkins and cider. If you're tired of walking or just want to explore, take a ride up the coast along Route 1. It's a beautiful drive
offering ocean views, autumn colors and plenty of restaurants. Don’t forget your camera.

A Little Lunch (or Dinner)

Once you’ve seen your share of leaves, consider a stroll into town for some of the area’s finest food and drink. For a genuine taste of Portland, check these out:


147 Cumberland Ave., (207) 772-0360
Offering a funky atmosphere, mismatched chairs, tinfoil ornaments, a little bit of Elvis and a solid menu featuring delicious pizza, shish kabobs and burgers.

The Kitchen

593 Congress Street, (207) 775-0833
A unique little restaurant with walls papered by local artists and other residents. Offers a pleasant atmosphere and huge bite for the money. Don’t miss the jerk chicken wraps, vegetarian delights and gyros.

But since you’re in Maine, why not go for some fresh lobster?

Lobster Shack

225 Two Lights Rd, (207) 799-1677)
Located just south of Portland in Cape Elizabeth.

Antiques, Galleries and Specialty Shops

Antiques, galleries and specialty shops scatter the Old Port and
surrounding city. Got a hankering for some window-shopping after lunch? Don’t miss:

Portland Antiques

223 Commercial Street, (207) 773-7052.
A unique shop offering nautical antiques, 18th and 19th-century furnishings and paintings.

Longfellows Antiques and Used Furniture

648 Congress Street, (207) 828-8699
Specializing in furniture, rugs, pottery, jewelry and toys.

Baxter Gallery of Portland School of Art

619 Congress Street, (207) 775-5152
A photograph and primary gallery housed in a beautiful old building located minutes from the Portland Museum of Art.


Whether you're a music buff, bar fly or just an average Joe,
there’s something for every SharpMan when the sun sets in Portland. For a full listing of live events and entertainment in Portland and surrounding towns, check out the Casco Bay Weekly or

Whatever your final destination, we suggest you begin your evening by strolling down Market Street for a sampling of tunes by local street musicians.

Once you’ve worked up a thirst, consider stopping off for a drink. Hailed as the microbrew capital of the Northeast, Portland’s Old Port and downtown areas have a nice selection of breweries and brew pubs featuring live local bands nearly every night of the week.

For beer die-hards with understanding (or beer-pounding) SharpWomen, consider taking a tour of the Shipyard Brewing Company (86 Newbury Street, (207) 761-0807, Geary's, Portland (claiming to be Maine’s first micro-brewery) or the Allagash Brewing Co.

To begin your search for your favorite of local brew pubs, sample:

Gritty McDuffs

396 Fore Street, (207) 772-2739
Located in the heart of the Old Port, Gritty McDuffs offers their famous fresh brewed beers along with live entertainment and tasty food.

Stone Coast Brewing Company

(14 York Street, (207) 773-2337)
Although part of a small chain of Maine pubs, this relaxed pub features a good choice of brews, an upstairs dining room and a dance area.

Also check out Sebago Brewing Company and the Seadog Brewing Company.

Romantic Places to Stay

Had enough? Time to hit the hay at one of Portland, Maine’s many beautiful, highly romantic inns or bed and breakfast. While there are too many to name here, we suggest beginning your search for the perfect one by reading SharpTravel’s How to Pick the Perfect Bed & Breakfast.

Getting There

If you're not sailing in by boat, or a stowaway on a cruise ship, then you’ll probably want to drive in (two hours from Boston, Massachusetts) or fly into the Portland International Jetport, (207) 774-7301, located just minutes from the heart of the city. Wanna know how much you’ll expect to pay? Check out airfare and car rental rates at SharpMan’s travel partner Travelocity for current fall specials.

More information
For more information on getting to and getting into Portalnd and other romantic destinations in Maine, check out .

This article last updated on Tuesday 12th October 2010
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