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…
Low Stakes
So much more than a steak house. All of their sauces are made in house, the chicken is grandma’s recipe, and their cake is to die for.
Crispy Gai
Simply the best fried chicken, Thai style. Hip and fun space. Bathroom selfies are a must.
Chaval
Upscale dining right around the corner. Spanish and French inspired, but mostly just magic. You can’t go wrong.
Scales
As the name might suggest they have a stunning array of seafood. But even as a seafood lover, sometimes I just have to have the pot roast. But no matter what you order, don’t skip the bread!
Twelve
Upscale big city dining in the small city. Prix fixe menu, or a la carte, the food is top notch.
Lucky Cheetah
Chinese cuisine like you’ve never had before. Wear your finest cheetah print for the best photo opportunities.
Flatbread
Local wood fired pizza, and when we say local, we mean it. There’s a map on the wall showing which ingredients come from each local farm. And ask for paper and crayons, and your drawing might end up on a menu!
Solo Italiano
Authentic Italian food, in a spectacular space, with plenty of interesting wines to pair!
Wilson’s County Barbecue
Carolina style bbq done right, along with a huge local beer list. Counter ordering so you can hang and watch the game!
Batson River
They distill their own spirits, they brew their own beer, AND they make an incredible meal. An elevated pub vibe, with a dedicated photo station. If you are here around the holidays, their holiday decor is not to be missed.
Fore Street
A Portland staple that never goes out of style. Menu that changes daily, specializing in local meats and seafood. And everything is cooked over wood fire!
Street & Co.
A Portland classic, with an exquisite all-seafood menu. With outdoor dining on Wharf St in the warmer months!
Hot Suppa
Southern style breakfast and lunch that won’t leave you hungry. We would never tell you to skip breakfast at the Chadwick, but maybe save a little room for brunch. They also have a nice patio in the summer!
Duckfat
Locals and tourists alike love Duckfat for good reason. Because duck fat makes everything taste better, both the restaurant and the ingredient. Paninis, fries, and milkshakes that are out of this world.
Gross Confection Bar
The most decadent and creative desserts and dessert drinks. No matter where you go for dinner, save room. And if you didn’t save room, make room. We believe in you. It’ll be worth it.
Eventide
Oysters and so much more. Creative sandwiches and rolls to share, and the one and only brown butter lobster roll. My personal favorite, and I’ve done a lot of “research”.
Portland Lobster
The most Maine experience, a giant lobster roll served on a dock. Live music and great beer. A seasonal staple.
Central Provisions
Creative and decadent small plates, made with local ingredients, in an open kitchen. Watching them make the food is almost as good as eating it. The key lime tart Zack gave me 10 years ago won my heart, so don’t skip dessert.
Pai Men Miyake
A cozy Japanese noodle house, with the most flavorful dishes. Do not miss the pork buns, although the tofu buns or lobster buns would be a close second.
The Green Elephant
An Asian bistro with all vegan/vegetarian fare. So flavorful, meat eaters beware, this food might change your mind.
Boda
An elevated Thai dining experience. Choose a traditional, and absolutely decadent beef Penang, or less traditional bacon wrapped dates. And dunk anything you can in peanut sauce.
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!