Portland, Maine is rich in spectacular dining and cultural opportunities, diverse recreational attractions, beautiful historical homes, a thriving small business community, and stunning natural beauty, making it a perfect sightseeing destination of New England.
Enjoy Dining, Shopping, Local Events & the Great Outdoors in Maine
Plan Your Stay with Our Portland Vacation Guide
With such a wide variety of things to do, you may never want to leave!
Keep scrolling to plan your perfect getaway.
Restaurants & Dining
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. Portland has more restaurants per capita than any other city in the United States! Here are a few of our favorites…
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!
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.
Copper Branch
Vegan; Walk-Ins Only
Serves plant-based, whole foods, that are good for you and the planet.
Breweries & Distilleries
Breweries and distilleries have multiplied substantially in recent years in Portland and throughout Maine. For an Essential Guide to Maine Breweries, check out Eater Maine. Below are our local favorites.
For a unique all-inclusive experience showcasing Maine’s booming craft alcohol scene, check out The Maine Brew Bus. These bright green school buses offer regularly scheduled and private tours in Greater Portland, with guides who give a behind-the-scenes look at Maine’s craft breweries, distilleries, wineries, and more!
Downtown Portland
The downtown area, known to locals as The Old Port, thrives with live music, dancing, shopping, dining, pubs, and famed microbreweries, and 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. Whether you’re looking for dancing, theater, live music, a drag show, or comedy, a stay at our bed and breakfast in Portland, Maine allows you to experience a variety of live entertainment right downtown.
The Great Outdoors
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.
- Casablanca Cruises
- Casco Bay Ferry Line Tours
- Greater Portland Landmarks
- Longfellow House
- Lucky Catch Cruises
- Maine Foodie Tours
- Maine Historical Society
- Maine Sailing Adventures
- Odyssey Whale Watch & Nature Cruises
- Portland Discovery Land & Sea Tours
- Portland Freedom Trail
- Portland Head Light
- Portland Sea Dogs
- Portland Trails
- Portland Walking Tours
- Spring Point Ledge Lighthouse
- Summer Feet Cycling
- Wicked Walking Tours
- Wine Wise Events
Museums & The Arts
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. 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 & Sightseeing
Maine offers great shopping and sightseeing in Freeport, Wiscasset, Rockland, Camden, Boothbay Harbor, and Bethel. 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!