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Portland, Maine's Historic Old Port Travel Guide

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Commercial Street | Portland's Historic Old Port | Portland Old Port guide
Portland's Old Port & Commercial Street

Use our travel guide to discover the salty wharves and cobblestone streets of Portland Maine’s historic Old Port. The waterfront neighborhood is the beating heart and (unofficial) center of Maine’s largest city. Old Port bustles with fishing piers, warehouses, seafood diners, boutiques, and bars waiting to be explored.

Old Port Portland Maineis a modern seaport that melds urban amenities with the charm of an 18th century neighborhood. The district’s brick buildings and busy piers are renowned for their cozy restaurants, lively waterfront, independent boutiques, and acclaimed brew pubs. Our Portland Old Port guide highlights favorite area attractions and things to do.

Brick Buildings of Portland's Historic Old Port | Maine Coast | New England
Brick Buildings of Old Port

Portland Maine's Historic Old Port At-A-Glance | Portland Old Port Attractions

Porthole & Boone's Fish House | Portland Old Port Restaurants | Portland Maine's Historic Old Port Travel Guide
Porthole & Boone's Fish House

For more information on Maine coast travel destinations read our articles on:

Shopping Portland's Old Port | Maine's Casco Bay | Free things to do in Portland Maine
Shopping Old Port


We recommend that you book lodging within Portland’s Old Port district. This location will allow you to park the car and walk to most areas and attractions (look for lodging with free onsite parking). There are a wide range of hotels in the city from budget chains, to boutique inns, to high-end luxury waterfront accommodations. Learn about Portland Maine hotels here.


Here is just a sample of the many things to do in Portland Maine:

  1. Take a walking tour of Old Port and the Waterfront

  2. Take a Donut Tasting Walking Tour of Portland Old Port

  3. Walk the Commercial Street wharves.

  4. Hike the 2.5-mile Baxter Trail from Portland’s Evergreen Cemetery to Back Cove

  5. Stretch your legs on the Eastern Promenade

  6. Take a guided RIB boat adventure on Casco Bay

  7. Embark upon a culinary walking tour of Old Port

  8. Take a Portland, Maine tasting tour of local brew pubs

  9. Take a trolley tour of the city

  10. Take an E Bike tour of Portland and its gorgeous coast

  11. Do a whale watch out on the Atlantic Ocean



Portland’s Old Port is located on Maine’s Casco Bay peninsula. Commercial Street is the main artery connecting cruising, fishing, and lobstering wharves with city blocks that house world-class shopping, eateries, and nightlife. Fore, Milk, Middle, Exchange, Market, and Silver are not-to-be-missed streets rounding out the area.

Cobblestone Streets | Portland's Historic Old Port Travel Guide | Maine Coast
Cobblestone Streets of Old Port

Situated on New England’s eastern seaboard, Portland has four seasons and a maritime climate. In the winter a few weather-dependent businesses close (think sea-going excursions), but most stay open throughout the year.

Once arriving in Old Port, it is best to park your vehicle and walk the area. There is metered on-street parking, but space is limited. There are many for-fee public parking garages. Make sure to explore the following areas:

Luke's Lobster Portland Pier | Portland Old Port Restaurants | New England
Luke's Lobster Portland Pier

Portland’s Commercial Street

Commercial Street is a historic artery that runs along the wharves of the harbor. The Old Port portion of the avenue runs roughly between the Casco Bay Ferry Lines and Becky’s Diner (.7-miles). However, along this stretch you can walk much further by exploring the many piers extending out into the sea. There are boat excursions, trolley tours, fish markets, restaurants, specialty stores, and bars crowding the wharves and Commercial St.

Portland's Commercial Street | things to do in Portland Maine |Maine Coast Travel Destination | New England
Portland's Commercial Street

Boothby Square and Surrounding Streets

Portland’s Boothby Square is Old Port’s central gathering space. The “square” is situated in a divided section of historic Fore Street. Surrounded by narrow cobblestone lanes, the park features an antique watering trough. Next to the granite trough, a lawn and bench are surrounded by taverns, local shops, and gourmet eateries. Boothby Square is a fun place to meet to take in the Old Port atmosphere. Silver and Market Streets shoot off of the square.

Boothby Square | Fore Street | Portland Old Port Guide
Boothby Square

Eastern Promenade

Located on Casco Bay at the edge of the Old Port shopping district (beginning around Casco Bay Lines) is the Eastern Promenade. This 78-acre city park has sweeping views of Casco Bay. There are walking paths, hiking trails, a beach, kayak rentals, a boat launch, picnic areas, ball fields, and a playground onsite (as well as a parking lot). The park is the site of many summer concerts, fairs, and festivals. It is a great place to get away from the bustle of the city and to enjoy beautiful views of the sea.

Harbor Fish Market | Things To Do in Portland Maine | Maine's Casco Bay
Harbor Fish Market


  1. Visit the Portland Museum of Art

  2. Take a seafood lovers walking lunch tour in Old Port

  3. Take a private island Fort tour on Casco Bay

  4. Tour the Victoria Mansion (A National Historic Landmark)

  5. See a Sea Dogs minor league baseball game at Hadlock Field

  6. Visit the Fort Williams Park and the Portland Head Light (lighthouse)

  7. Take a cruise on the Portland Tall Ship in Casco Bay

  8. Enjoy a tour of Portland's lighthouses


East End Beach

(Cutter Street, Portland)

Located at the end of Cutter Street in the Eastern Promenade park there is a beach with onsite parking. Facilities at the beach include restrooms, changing rooms, a boat launch, and kayak rentals. There is a grassy hill behind the beach for picnicking and sunbathing. The small, picturesque, pebble beach is the only public beach within Portland city limits.

Crescent Beach

(66 Bowery Beach Road, Cape Elizabeth, Maine)

About 8-miles south of Portland sits Crescent Beach State Park. A beautiful 1-mile crescent shaped sandy beach is the park’s centerpiece. Onsite are picnic tables with grills, a playground, snack bar, changing rooms, and restrooms. The park also features a nature trail through grassy dunes and woods. Open seasonally.

Commercial Wharves | Portland Old Port Guide | Maine Casco Bay
Commercial Wharves

Old Orchard Beach

(Old Orchard Beach, Maine)

Some 20-miles south of Portland on the Maine coast is the 7-mile long Old Orchard Beach. This gorgeous white sand beach is a popular spot for sunbathing, swimming, surfing, jet skiing, volleyball, and beach combing. In the adjacent beach town, visitors will find the Old Orchard Pier (extending 500 feet out into the Atlantic Ocean). The pier is full of restaurants, shops, and arcades. In addition, the Palace Playground amusement park offers classic kiddie and thrill rides.

 Portland Sea Bags | Maine coast vacation destination | New England
Portland Sea Bags


Portland has a well-earned reputation as a foodie-mecca. Gourmets in-the-know consider the city to have some of the best restaurants in the world. Not every eatery is expensive, though, nor is the great food scene exclusive to fresh seafood. Portland boasts an impressive, eclectic array of diners, bakeries, cafes, breweries, and restaurants for all budgets.

Custom House | Portland's Historic Old Port Travel Guide
Custom House

Long-time Portland Old Port eating-establishment favorites include Duckfat (European sandwich shop and cafe), Central Provisions (small plates and cocktails), The Holy Donut (craft donuts and desserts), DiMillo’s on the Water (Seafood), Evantide Oyster Company (American Oyster Bar), the Honey Paw (Korean), and the Standard Baking Company (breads and pastries).

Hope you enjoyed meeting the Maine-ahs, Laura and Randy

Simon Pearce Window Display | Portland Old Port Guide  | Free things to do in Portland Maine
Simon Pearce Window Display

For more information on Maine coast vacation destinations read our articles on:

Commercial Street Wharves | Portland Old Port Attractions
Walking Portland's Wharves


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