Portland, Maine: What to Do

Portland Maine is a beautiful waterfront city that sits on a peninsula extending into Casco Bay. Filled with red brick buildings, delicious restaurants, and beautiful shops – many of which are filled with local artists’ creations – this is a great getaway  whether you live in New England or are flying across the country.

Read on to get my recommendations for where to stay, eat, and what to do in Portland, Maine!

Where to stay:

  • Hilton Garden Inn. This hotel is in great location, sitting in the Old Port by the water.
  • Portland Regency. This hotel sits in the middle of the city. The perfect jumping off point for walking to restaurants and shops.

Where to Eat: Known for being a “foodie” city, almost any restaurant choice is a good one! Here are a few I have been to and recommend.

  • Central Provisions
  • Flatbread
  • Standard Baking Co. for fresh baked bread
  • Little Tap House
  • Duckfat
  • Fore Street

What to Do: 

  • Walk through Old Port.
  • Take a firetruck tour.
  • Get a donut at Holy Donut. Made with Maine mashed potatoes, these donuts are the most moist and delicious donuts I’ve ever had.
  • Go shopping on Exeter Street. Make sure to stop by Earthbound Trading, Gus & Ruby Letterpress, Lisa-Marie’s Made in Maine, and Maxwell’s Pottery Outlet.
  • Visit Portland Head Lighthouse. About 15 minutes outside of the city, the lighthouse has a museum and is surrounded by hiking trails. See pictures below!
  • Stop and get a cocktail at Vena’s Fizz House. Small and intimate, this bar is more of a chemistry lab than a bar. They are experts in bitters, housemade soda, and mixing creative cocktails.
  • If you like beers, check out the many breweries in the city including Allagash, Rising Tide, Bissell Brothers, and Sebago Brewing. Another option is taking the Maine Brew Bus (I’ve taken two so far and both have been great!). You buy tickets beforehand for a specific tour and they drive you to local breweries with a small group of anywhere between 2-15 people. On the two tours we took we stopped at Dirigo, Banded Horn, Barreled Souls, Nonesuch, Island Dog, and Yes Brewing.
  • Go to Cellar Door Winery.
  • If you want a lively bar crowd, head to RiRa after dinner for local live bands and plenty of drinks.
Portland Head Lighthouse
Portland Head Lighthouse
Portland Head Lighthouse
Portland Head Lighthouse

Portland, MaineOld Port

Bissell Brothers
Bissell Brothers Brewery


Portland, MaineHoly Donut

Holy Donut
Holy Donut
Portland Maine
Exchange Street

portland 16

Vena's Fizz House
Vena’s Fizz House Store

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