Maine is the type of place that you want to tell people about, but at the same time it is a place that you don’t want everyone to know about for purely selfish reasons. A sleepy town with a thriving creative scene, a visit to Portland strikes a delicate balance between a desire for you to hit the twitters with “Portland is amazing” in the same way visitors to places like Austin and Nashville do, with a selfish inclination towards covertness. Even as the Pine Tree state’s biggest city, Portland is a relatively small place that is easy to get to know. A quaint respite from the frenetic pace of the rest of the East Coast, it’s a town where hardworking blue collar folks embrace good food and a laid back way of life. Only just a small city, from dining to shopping, Portland is an aesthete’s dream.


1. Portland in the summertime is a different beast than Portland in the “off season”. The Old Port in summer is the province of the gray-haired cruise ship-set. Best to limit your time there to a day or two. Better yet, in the summer use Portland as a launching pad to a relaxing jaunt Down East.

2. Expect to eat well. For a city its size, the Portland food & wine situation is extremely rich.

3. Everyone needs to visit the L.L. Bean flagship at least once in their life. Since 1953 is has been a 24/7 operation, so don’t be afraid to go buy some “Boat & Tote” in the middle of the night.

4. Be sure to explore. Maine is a rich place with lots of nooks and crannies just waiting to be discovered.

5. The locals are nice, you should be too.

Petite Jacqueline

Friendly French food, Petite Jacqueline is a playful spot that is equal parts neighborhood eatery and culinary destination. It’s casual and precious in a way that keeps you in a state of engaged relaxation. The menu is well structured from both land and sea. The wine list is diverse, but also manageable and well thought out with a strong offering of wine from some of France’s lesser known appellations. It’s Maine meets France in the best way possible.


Part art gallery, part clothing label and part pop-up specialty shop, Seawall puts a new and creative spin on your typical retail space. The hybrid shop was founded by Daniel Pepice, Sara Lemieux, Thom Rhoads and Brook Delorme in the spring of 2012 with the idea of showcasing the best Maine had to offer from the worlds of clothing, art and accessories. Seawall also stocks great product from other designers that serves to compliment the in-house label and local goods. It’s a worthy destination for those with an interest in creative things made with care.

Becky’s Diner & Co.

In a world of egg whites and spinach, Becky’s is the place to skip the healthy stuff and celebrate the classic American breakfast in all of its caloric glory. A destination for fisherman in search of post-catch sustenance (Portland is one of the U.S.’s oldest working ports) Becky’s is the type of place where the waitresses walk around to faithfully “warm up” your coffee and chat. Casual and satisfying, Becky’s is the place to start your day in Portland.

Portland Dry Goods

Situated perfectly on Commercial Street in the Old Port, Portland Dry Goods (a new addition to the Portland shopping scene) is the place to find the hardworking brands that made waxed canvas and buffalo plaid cool again. Labels like Engineered Garments, GANT, Red Wing, Woolrich John Rich, plus all sorts of other great classic American menswear including a nice offering of handsewn shoes from local favorite Rancourt & Co. It’s the perfect place to shop if you are looking for clothes that stand the test of time.

Winslow Homer Studio (Portland Museum of Art)

Not one to enjoy the company of others, Winslow Homer famously built his Prouts Neck studio with no windows facing the street, so that way he could paint in peace and wouldn’t have to actually come into contact with anyone. The most striking quality of the wood shingled studio — which has recently been beautifully restored by the Portland Museum of Art — is its wonderful ability to frame Maine’s natural beauty, surroundings that helped make Homer and his landscapes famous.

Street & Co.

Less is more at Street & Co. The conceit for this beloved restaurant is to pair local food with Mediterranean flavors using low tech preparation methods to create simple honest food. It’s a model often attempted and rarely successful, but at Street & Co. it’s a combination for success. Expect captivating offerings of seafood that comes straight off the boat from local fisheries. Expect seasonal vegetables and delicious pastas. Expect to walk away with a deep respect for the Portland culinary scene.

David Wood

A celebration of some of the region’s finest clothiers including shirts from New England Shirt Co.(Fall River, Massachusetts), shoes from Alden (Middleboro, Mass.) and suits from Southwick (Haverhill, Mass.). David Wood is an old school men’s shop that celebrates quality and service before all else. In an era of fast and cheap, David Wood is like a window into a world of high standards and quiet sophistication.

Fore Street

The wonderful smell of wood burning in the stone and brick hearth at the center of the action at Fore Street permeates the entire restaurant. At Fore Street they have been serving farm to table food — along side a diverse wine list — since 1996, long enough to give the Portland eatery status as one of the best in the state, and as one of the most enjoyable dinners in America.

Cape Porpoise Outfitters

Opened the summer of 2012, Cape Porpoise Outfitters is writer Jared Paul Stern’s extension into the physical viava beautiful red 1880s livery stable in quaint Cape Porpoise, Maine. CPO offers an ever changing selection of men’s-focused vintage clothing, Americana, military surplus, furniture, art with some new items like bags from Norwegian-sea- faring supplier Helly Hansen. Mixed in amongst the massive stock of interesting objects and oddities in a celebration of East Coast prep culture. When you are done shopping for things you never knew you needed, stop into the Cape Porpoise Kitchen for a glass of rosé and lunch with the locals.


Ask around and most people say that shoemaking in Maine is all but extinct, largely a victim of cheap labor overseas. This is true in most places, but it is certainly not the case outside of Portland in Lewiston at the family-owned Rancourt & Co. shoe factory. The Rancourt family has been making handsewn shoes using traditional methods for three generations. On a given day at Rancourt & Co. men and women work with their hands to individually craft some of America’s finest shoes from Camp Mocs to Beef Roll Penny Loafers — right in the heart of Maine. Keeping traditions alive never looked so good.