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Things To Do

Portland is one of the best coastal cities in New England (in our opinion!) and September is the best time to come! Known for its restaurant scene, Portland has incredible restaurants, bakeries and breweries. We've included some of our favorite places to eat and walk, but you really can't go wrong. September is also one of Portland's busiest seasons, so we highly recommend making restaurant reservations if you're coming for the weekend.

Standard Baking Co

75 Commercial Street, Portland, ME 04101

One of our favorite spots for baked goods. Make sure you go early - there will be a line!

Bread & Friends

505 Fore Street, Portland, ME 04101

Great baked goods and brunch. Claire especially loves their creative coffees.

Speckled Ax

18 Thames Street, Portland, ME 04101

Great local coffee shop close to the harbor walk. We went here after we got engaged on our morning dog walk!

Tandem Coffee and Bakery

742 Congress Street, Portland, ME 04102

One of our favorite coffee shops with the best baked goods. Their Congress Street location has a great outdoor seating area, but be prepared to get there early and stand in line. They also have a location on Anderson Street if you're willing to make a short drive.

Luke's Lobster Portland Pier

60 Portland Pier, Portland, ME 04101

Best spot in downtown Portland to grab a lobster roll on the water.

The Highroller Lobster Co.

104 Exchange Street, Portland, ME 04101

Fun diner/lobster pound vibe. It's popular spot, so go early and get the lobster roll flight!

Scales

68 Commercial Street, Portland, ME 04101

Currently the queen bee of nice dinners in Portland. Great seafood and atmosphere on the water. Make your reservations early!

ViA VECCHiA

10 Dana Street, Portland, ME 04101

One of our favorite restaurants and great Italian food. Claire would say get a window table in the front. Dixon says head to the back bar!

The Honey Paw

78 Middle Street, Portland, ME 04101

Asian small plates restaurant next door to and by the same owners as Eventide. Honestly, we like it more!

The East Ender

47 Middle Street, Portland, ME 04101

Cozy pub with great food and a late-night karaoke scene. We think it's a hidden gem. Ask for a table upstairs and get the fried deviled eggs.

Wayside Tavern

747 Congress Street, Portland, ME 04102

If you want a nice dinner out of the Old Port, Wayside Tavern is a cozy, refined atmosphere with a great seasonal. This is where we had our wedding dinner!

Cuties

46 Market Street, Portland, ME 04101

Claire's favorite cocktail bar. Located right in the center of the Old Port. Super fun and funky and lots of yummy bar snacks.

Room for Improvement

41 Wharf Street, Portland, ME 04101

A cocktail bar dressed like a dive bar. The brother property to Cuties, they have great cocktails, beers and hot dogs.

Ruski's Tavern

212 Danforth Street, Portland, ME 04101

For the SLU crew.

Stroll Around the Old Port

Portland, ME 04101

The Old Port is Portland’s historic waterfront district, known for its cobblestone streets, working wharves, and lively mix of boutiques, bars, and standout restaurants. It’s the perfect place to wander, grab a drink, and soak in the coastal charm.

Take a Walk on the Narrow Gauge Railroad

65 Thames Street, Portland, ME 04101

A popular running and walking path along Portland's historic narrow gauge train tracks, with beautiful views of Casco Bay and a little beach if you're brave enough to dip your feet in the ocean.

Hang out on the Eastern Promenade

Eastern Promenade, Portland, ME 04101

Head up to Munjoy Hill on the Eastern Promenade for panoramic views of Casco Bay and grab a bite to eat at one of the food trucks (highly recommend Falafel Mafia!)

Visit the Breweries on Fox Street

Bop around some of Portland's best breweries on Fox Street (a 5min drive from downtown) including Austin Street, Rising Tide, Belleflower, Apres (spiked seltzer), Orange Bike and Blue Lobster Winery.