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The city of Portland, Maine is the largest in the state, but with all the charm of a classic seacoast town. While the city is a congregation of historic waterfront, art communities, coastal lighthouses, hole in the wall pubs, top chef restaurants, sidewalk performances, antique and art shops, and nightclubs, it retains a "small town" feel. There is so much to see and do depending on how much time you plan to spend in Portland. Between shopping, exploring the Old Port, gourmet dining, historic tours and boat rides, there is truly something for everyone to enjoy!
The Old Port district is known for its chic boutique shopping, renowned dining and bustling nightlife. Old Port shopping includes exquisite crafts from local artists and designers. The charming Old Port is a successfully revitalized warehouse district with cobblestone streets, old brick buildings and quaint fishing piers. Old bank and warehouse buildings have been transformed into shops, apartments, restaurants and office spaces with original and unique architectural features. Take a walk along Commercial Street and experience one of the few working waterfronts left in the United States. At night and on the weekends, the Old Port comes alive with entertainment and nightlife at the many bars, brewpubs and event spaces in the area.
Things to do in Portland
If you have time to spare during your time in Portland, there is much surrounding area to explore by boat. The Casco Bay Ferry Lines located right in Portland Harbor can take you to beautiful nearby islands for day trips or sunset cruises. The Casco Bay Ferry Lines run year-round and travel to Peaks Island, Little Diamond Island, Great Diamond Island, Diamond Cove, Long Island, Chebeague Island, Cliff Island or Bailey Island. All of these islands offer something different, from scenic hiking and biking trails to small beaches and ocean view dining. Sunday Reggae Fest at Peaks Island is a very popular afternoon of music, dancing and drinks at Jones Landing Restaurant and Bar reached by Casco Bay Ferry. There is lodging on these Casco Bay islands, Inns on Peaks Island, Chebaque, Long Island and Great Diamond Island. From Portland Harbor, visitors are also able to explore the sea on private sailing charters or beautiful sunset or sunrise cruises.
Nautical buffs will enjoy a visit to the Portland Observatory, located on Munjoy Hill. Built in 1807, the observatory is the last wooden signal tower in North America. It is also one of the few structures that survived the Great Fire of 1866 that devastated much of Portland. The observatory offers great views of Portland, Casco Bay, Back Cove and Mt. Washington. It is owned and operated by the City of Portland and Greater Portland Landmarks, who offer guided tours during the summer season.
Portland is also known as a cultural hotspot for artists. The Arts District of Portland is located on much of Congress Street, towards the West End. Here, visitors will find many art galleries, museums, theaters and even the Maine College of Art. The First Friday Art Walk occurs on the first Friday of every month, when local galleries and museums are open to the public with free food and drink. The Portland Museum of Art is the largest and oldest art institution in Maine, designed by renowned architect IM Pei.
For sports enthusiasts, a Portland Sea Dogs baseball game is fun for the whole family. As the minor league affiliate to the Boston Red Sox, Sea Dogs games draw fans of all ages to cheer on future big leaguers and watch some impressive baseball. Tickets are extremely affordable and there is always something fun going on at Hadlock Field from contests and giveaways to games and entertainment from Slugger the Sea Dog, the team's mascot. Former Sea Dogs players include Jacoby Ellsbury, Kevin Youkilis, Dustin Pedroia and Kevin Millar. You may spot current Red Sox stars playing in a Sea Dogs game, like Dice K, as they rehab on their return to the Major Leagues.
There are plenty of affordable lodging options in Portland including chain hotels, quaint bed and breakfasts and renowned historc inns in the downtown area, and in South Portland near the Maine Mall and Portland Jetport. If you are feeling adventurous, you can stay on a Portland island for a night, arriving and departing by boat. Whether you are visiting for a day, a week, or longer, you will never run out of things to do, see and eat in Portland! With a population of about 66,000 in Portland it's quite manageable and very Maine. In fact, a quarter of Maine's total population is in greater Portland, 230,000 of Maine's million + residents. Learn more about Portland hotels.
Even if you only have one day in Portland, dining at a world-renowned restaurant is an absolute must. Portland was voted America's Foodiest Small Town by Bon Appetit Magazine for its many different restaurants, each serving up unique and delicious plates for your tasting pleasure. Portland restaurants have everything from fresh seafood, raw oyster bars and mouthwatering lobster to Italian, Irish, pizza, Asian and Mexican. Choose to dine by the water at several choice restaurants including DiMillos which is a floating boat restaurant or one of the smaller, charming Old Port settings with exposed brick walls, high ceilings and windows or more modern fixtures. Portland offers Maine Foodie Tours for those who are only in town for a short time but would still like to experience all the culinary delight. For beer lovers, Portland has the highest concentration of microbreweries in the country, with many offering tours and tastings.
No trip to Maine is complete without visiting an authentic Lighthouse and Portland has many to choose from. Portland Headlight is one of the premier lighthouses in America and also one of the oldest, commissioned in 1791 by George Washington. The Headlight is located in Fort Williams Park, a popular location for picnics, hiking, relaxing in the park or visiting the museum built in the former Lighthouse Keeper's quarters. From Portland Head Light, you can also view Ram Island Ledge, a 77-foot granite conical tower a few miles offshore. Spring Point Ledge resides on the west side channel of Portland Harbor and is popular amongst visitors who are able to walk the breakwater rocks to the 54-foot cast-iron tower. Portland Breakwater Light, called Bug Light by locals, guides ships from Casco Bay into Portland Harbor. If you have time, head down to Cape Elizabeth to visit Two Lights, named for its views of East and West Light.
At night, the city of Portland is bustling with locals and visitors who have come to enjoy the city nightlife. Portland is full of sports bars, cocktail lounges and nightclubs offering something different for everyone whether you choose to sip a beer and enjoy the game, chat with old friends over cocktails in a wine bar or dance to some of the hottest local DJs spinning music all night. Local venues also provide space for talented musicians to play, from local bands to more well known names that sell out the Cumberland County Civic Center. Portland also attracts hilarious comedians like Maine's own, Bob Marley who perform at local venues, including the popular Comedy Connection, located dockside on the harbor.