Our Top Portland, Maine Recommendations

“City worldliness with a small-town-feel” best describes Portland, Maine. Being one of the country’s most longstanding and busiest seaports, Portland is rich in historical homes and small businesses, making it a perfect historical sightseeing destination. Portland features spectacular dining and cultural opportunities, as well as diverse recreational attractions and stunning natural beauty. With such a wide variety of things to do, you will never want to leave!

Many visitors come to the city because of the great buzz surrounding the contemporary cuisine cooked fresh in many of the 300+ restaurants within the city limits. Numerous Portland chefs are nominated each and every year for the highly coveted James Beard Award. Long known as a local seafood capital, Portland has a new reputation for contemporary cuisine prepared by talented chefs.

The downtown area, known to locals as The Old Port, thrives with live music, dancing, shopping, dining, pubs, and famed microbreweries is one of the most successfully revitalized warehouse districts in the country. Enjoy a walk on one of the many wharfs, stroll down the cobblestone streets, and enjoy boutique shopping by day and vibrant live music by night.

A few blocks uptown of the waterfront is Portland’s secret treasure, The Arts District. With Congress Street as its spine, this once traditional shopping street has turned into a mecca of art galleries, antique shops, artist studios, and trendy restaurants. All this is just walking distance from the inn.

The stunning natural beauty of the Maine coast lends itself to many outdoor activities. Hiking, cross-country skiing, swimming, sailing, biking, golfing, canoeing, kayaking, and state parks can all be found within 15 minutes of The Chadwick Bed & Breakfast. Portland offers some of the best water access to the islands of Casco Bay, historic forts, and lighthouses. You can easily plan a day trip that includes water view, the rugged coast, and picturesque mountain regions, all in the proximity of Portland.


Visitors also come to Portland to experience some of the wonderful cuisine offered in 300+ restaurants scattered throughout the city. Portland has more restaurants per capita than any other city in the United States! Here are a few of our favorites:

  • Chaval – European-American; Reservations Suggested
    A local favorite, close to the inn. Spanish + French-inspired seasonal cuisine. Ask to eat outside when the weather is nice!
  • Katahdin Wood Fire Grill & Bar – Contemporary American; Reservations Suggested
    New menu every night! Panzanella salad, amazing cocktails, lovely people. Perfect spot if you’re eloping in Portland!
  • Local 188 – Spanish / Mediterranean / Tapas; Reservations Suggested
    Close to the inn, open seven days a week. Meatballs, seafood paella, and a wine bar.
  • Fore Street – American; Reservations Suggested Well in Advance
    It remains one of the most recognized and talked about restaurants in Portland – so be sure to make your reservation well in advance.
  • Street & Co. – Seafood; Reservations Suggested Well in Advance
    An extremely knowledgeable wait-staff and the best seafood meal you will ever have, hands-down.
  • Paciarino – Italian; Reservations Suggested
    Open 7 days a week during the high season, serving authentic Italian food. Everything is delicious—like grandma made it herself.
  • Hot Suppa – Southern Kitchen; Walk-Ins Only
    Hearty Southern fare and comfort food all from scratch. Including our favorites Chicken & Waffles and the Fried Green Tomato BLT.
  • Duckfat – Sandwich Shop; Walk-Ins Only
    Panini sandwiches and local Belgian fries fried in duck fat… enough said.
  • Gross Confection Bar – Dessert Bar / Craft Cocktails / Bakery; Walk-Ins Only
    Amazing dessert confections that we’re sure you’ve never seen on a menu before! Bakery by day and dessert + cocktail bar by night.
  • Salvage BBQ – Barbeque; Walk-Ins Only
    Located close to the inn. You can smell the smoke shack from a half mile away! They have 16 taps that feature Maine microbrews. Order at the counter and they’ll find you when your food is ready!
  • Eventide Oyster Co. – Seafood / Oyster Bar / Small Plates; Walk-Ins Only
    When Alton Brown of Food Network fame says it’s the best oyster bar he’s ever eaten at in his life, they must be doing something right!
  • Portland Lobster Co. – Seafood; Walk-Ins Only (Open May-October)
    Hands-down, the best and biggest lobster roll in town. Great outdoor seating and live music most of the time.
  • Central Provisions – Small Plates; Walk-Ins Only
    Drinks in punch bowls and a menu you’ll want to keep at the table until you’ve tried everything. Great selection of local brews.
  • Pai Men Miyake – Ramen Noodle Bar; Walk-Ins Only
    Ramen, pork buns, Brussels sprouts—order all the food.
  • The Green Elephant – Vegetarian Bistro; Walk-Ins Only
    Even for the meat-lover, you’ll never finish a meal disappointed!
  • Slab – Sicilian Street Food; Walk-Ins Only
    Until you’ve had their Sicilian slab, you just haven’t lived.
  • Boda “Very Thai” Kitchen + Bar – Thai-American Fusion; Walk-Ins Only
    Open very late, serving till 12:45am every night. With amazing flavors and so much to choose from, this is a local favorite.

Brewery & Distillery Tours

Brewery and distilleries have multiplied substantially in recent years in Portland and throughout Maine. Come sample and enjoy some of the best brews and spirits in the nation! For an Essential Guide to Maine Breweries, check out Eater Maine. Here are some of our local favorites:


With so much to do right downtown, you’ll want to extend your stay! Whether you’re looking to experience Portland via guided tour, peruse Downtown Portland’s history, enjoy the beauty of our lighthouses, or cheer on a sports team, there is a wealth of activities to meet your expectations.


Along with a thriving arts scene, Downtown Portland offers museums and galleries, each with their own impressive collections of artists, paintings, and other artistic works that would appeal to any art lover.


Shopping and retail go hand in hand. Here you will find a list of local retailers of all types from fashion to food, arts and crafts, to sporting goods, furniture, collectibles, and so much more—there’s a lot to shop for! Check out the websites below for comprehensive lists and up-to-date information on retailers, promotions, and sales in the Greater Portland area!


Whether you’re looking for dancing, theater, live music, a drag show, or comedy, Portland allows you to experience a variety of live entertainment right downtown.


Many of our guests want to continue their regular exercise routines while in town. We want to help you look and feel your best, so we’ve listed some local options for indoor exercise.


Portland’s peninsula is a great part of the city for walking. If you want to venture further than your feet or energy will take you, there are METRO Buses and reliable Uber Ride Share Service to keep in mind before renting a car. When guests ask whether or not they should rent a vehicle, we really leave that decision to their own preference.

For those who want to walk: from The Chadwick Bed & Breakfast, it is 10-15 minutes to The Arts District, 20-25 minutes to The Old Port, and 30-40 minutes to destinations on The East End.

For driving directions to The Chadwick Bed & Breakfast or directions from the train station, airport, bus station, or harbor, please click here.


Portland’s weather can be unpredictable. Typically, Portland experiences temperate springs and sunny summers, as well as crisp colorful falls and snowy white winters. If you are looking for one of the four seasons, Portland is the town to come to!

A long-term weather forecast of Portland is likely to change, so you may not find it as accurate as planning a few days in advance. We always suggest that you consult the weather forecast in Portland a day or two before you arrive. Sudden showers and higher-than-expected temperatures, as well as cool nights, have caught many Portlanders off-guard from time to time. Our advice is to pack a few layers (for any time of the year), comfortable shoes, and some rain cover (we provide umbrellas).

For Portland weather throughout the year, such as average temperatures and precipitation, visit The Weather Channel.

Beyond Portland

Outside of the city, Maine offers great shopping and sightseeing in Freeport, Wiscasset, Rockland, Camden, Boothbay Harbor, and Bethel. Fishing, boating, camping, and hiking are a short drive away in the beautiful Lakes Region and the Western Foothills. Leaf-peeping in the autumn—when the landscape is colored with the warm glow of red, orange, and yellow—is always stunning for locals and visitors alike. In the winter months, skiing, snowboarding, and snowmobiling are not too far from The Chadwick Bed & Breakfast.

All this, plus the White Mountains of New Hampshire and the historic city of Boston are just a stone’s throw away. With all that the region has to offer, you might ask to extend your reservation!