Travel, Weekend Unexplored
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Weekend Unexplored: Portland, Maine and surrounding area

Portland, Maine, is a quick 2 hour drive north of Boston, making it a perfect weekend trip.  My husband and I fell in love with Maine few years ago, especially Portland and its surrounding areas.  You can find beautiful scenic sights, plenty of outdoor activities, antiquing, great food scene and, of course, lobster rolls.  After so many years, we have perfected our weekend trip itinerary and where to take our “out of town” guests.  Here are some of our favorites and make sure to also scroll all the way to the end for our sample weekend itinerary.


The Press Hotel (119 Exchange St, Portland, ME 04101) Website


Source: Instyle

*If you are a history buff, then Press Hotel is a must stay.  The hotel used to be the Gannett Building that housed the offices and printing plant of the Portland Press Herald.  The building was converted to a hotel after the newspaper shut down in 2010.  The hotel has vintage-styled furniture juxtaposed against contemporary interiors and playful newsroom references making it my favorite hotel in Portland.

The Portland Regency Hotel & Spa (20 Milk St, Portland, ME 04101)Website


Source: the Regency

*For the romantics, the Portland Regency Hotel is a wonderful 19th century armory converted into a hotel.  The hotel is situated in the heart of Old Port district and also 2 blocks from the waterfront.  The hotel and rooms have “a bed & breakfast, old world” aesthetic. We stayed here when we were on our honeymoon.


My husband summed the Portland’s dining scene up perfectly.  In his words, “A bunch of tattooed, creative chefs decided to migrate to Portland for the “farm to table” or “nose to tail” ingredients and a hipster environment to experiment their crafts.  The result is high, innovative food at a reasonable price and no false pretense dining experience.”  There are amazing selections of high quality restaurants in Portland to satisfy the foodie in all of us.  Below are our favorite restaurants that we keep coming back year over year.

DINNER – Miyake (468 Fore St, Portland, ME 04101) Website


Source: the owner

*This Japanese restaurant focuses on high quality ingredients sourced around the world but places heavy emphasis on locally sourced ingredients and from their own farm.  The dishes are inventive and infused with Japanese, French and Italian techniques.  Their omakase is a must!

DINNER/LUNCH – Central Provisions (414 Fore St, Portland, ME 04101) Website


Source: the owner

*Central Provision is a new addition to our list of restaurants to visit in Portland.  The restaurant is housed in a historic brick building in Old Port.  All the dishes are small plates and very inventive.  We loved everything that we ordered and their cocktails are also a must try.

DINNER Hugo’s Restaurant (88 Middle St, Portland, ME 04101) Website


Source: the owner

*Hugo’s has been on our list as one of the top restaurant on the East Coast.  It blew us away several years ago and we always made a point to dine at the restaurant every time we visit Portland.  They have changed chefs and menus in the past few years and with greater Asian influence.  It’s definitely still worthy of being one of the most innovative restaurant in Portland but we somehow feels the food has not “wowed” us as before.



Source: Weare Sweet

*This wine store converted into a wine bar last year.  They have a great selection of natural wines to try with a light bite before you head to dinner.

LUNCH – Duck Fat (43 Middle St, Portland, ME 04101) Website


Source: the owner

*Duck Fat is a European-style Sandwich Shop near Hugo’s.  The former Hugo’s owner and chef created this shop to focus on local sourcing.  They are famous for their Belgium-style French fries, fried in duck fat, milk shakes and sandwiches.

BRUNCH – Bayside American Café (98 Portland Street, Portland, ME 04101)  Website


Source: the owner

*This local institution is famous for their brunch that features local ingredients with global influences.  Some favorite dishes include Maine Crab Cakes and Lobster Frittata!

BRUNCH – Palace Diner (18 Franklin St, Biddeford, ME 04005) Website


Source: the owner

*This diner is housed in a vintage counter-serve diner car, located outside of Portland.  They served old-fashion comfort eggs and pancakes.  For those looking to recapture 1940-50’s era, this diner is a must try.


Red’s Eat (41 Water St, Wiscasset, ME 04578) Website


Source: La Vie Partagee

*My husband and I have tried so many lobster rolls over the years.  We have done more than our fair share of lobster roll crawls around Maine.  Red’s Eat consistently beats out the competitions and we always go to this lobster shack on the edge of Sheepscot River in Wiscasset every visit.  Be prepare for a really long wait if you arrive after 11am but it is worth it!  Our staple order consists of 2 lobster rolls, fried clams, fried oysters and blueberry pies.


Blue (650A Congress St, Portland, ME 04101) Website

*Intimate live music venue with variety of music every night and Jazz on Saturday

Portland House of Music and Events (25 Temple St, Portland, ME 04101) Website

*This music venue is small and has a very eclectic list of performers.  You can normally walk in for a few dollars.


Old Port Website


Source: Octavias Vintage

*This is the oldest section of Portland with its cobblestone streets and 19th century brick buildings and fishing piers.  The buildings have now been converted to restaurants and boutiques.

Maine Narrow Gauge Railroad Co & Museum (58 Fore St, Portland, ME 04101) Website


Source: Press Herald

*Small, fun railroad museum featuring box cars and relics from the late 19th century and early 20th century.  It’s a fun experience to take a ride in the vintage train along the 1 ½ mile railroad tracks along the waterfront of Casco Bay.

Pemaquid Point Light House (3115 Bristol Rd, Pemaquid, ME 04558) Website


Source: Yahoo Pic

*The 1827 light house is our favorite Maine lighthouse to take our guests to visit.  It houses a small museum and you can wander around the site to take in the waves crashing along the bluff.

Two Lights State Park (7 Tower Dr, Cape Elizabeth, ME) Website


Source:  Boom Beat

*This lighthouse is situated on a picturesque bluff with the most spectacular view.  It’s a short drive from Portland and a great first stop on your light house tour.  There are picnic areas to lounge around and you can grab a lobster roll at the Lobster Shack on site.  They make serviceable lobster rolls.

Damariscotta Pumpkin Fest Website  – Columbus Day weekend


Source:Life Is Mine

*If you are in town during Columbus Day weekend, the Pumpkin festival in Damariscotta is a must visit.  Local Maine artists decorate approximately sixty to seventy Atlantic Giant Pumpkins which are displayed in downtown Damariscotta & Newcastle.  It’s a fun, family-friendly experience to stroll down Main Street and see all the pumpkins.

Our weekend trip itinerary for Out of Town Guests


  • Check into your hotel
  • Grab a pre-dinner drinks at Drifters Wine
  • Head to dinner at one of the restaurants listed above. These are wildly popular restaurants so be sure to get reservation in advance.
  • Check out the music at Blue or Portland House of Music and Events
  • Night cap at the Press Hotel lobby bar


  • Drive to Pemaquid Lighthouse early in the morning
  • Return to Red’s Eat for lobster rolls, fried clams, fried oysters and their famous blueberry pie!
  • Walk around Wiscasset and visit the unique boutiques and antiques stores
  • Drive to Kennebunkport, Maine
  • Drive along Ocean’s Drive to see the scenic ocean view and mansions
  • Get out of the car at Walker’s Point to see the Bush Compound
  • Take a late afternoon break at the Spirit Restaurant
  • Grab early dinner at one of the local restaurants in the area or head back to Portland for dinner


  • Brunch at one of our reccomended breakfast/brunch places on the list
  • Head to the Maine Narrow Gauge Railroad Co & Museum
  • Visit the boutiques and shops near the waterfront for gifts to take home
  • On your way back to Boston, do a quick stop at Two Lights State Park for the perfect New England picture and a lobster roll for the road

Featured image: Flickr User: Wendell

For related articles, visit the TRAVEL page.

Author: Thai-Anh Hoang

1 Comment

  1. Julie says

    Wow Thai An this is super helpful. I really appreciate all the thought you put in to this. Will def be checking out a few suggestions. Esp Miyake!


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