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16 Mar 2025Updated last time
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Portland Maine Itinerary

Portland, Maine Highlights Itinerary Overview

Discover the charming and historic city of Portland, Maine with this specially curated itinerary. Begin your journey in the iconic Old Port, where cobblestone streets and 19th-century brick buildings create a nostalgic atmosphere. This vibrant waterfront district is renowned for its eclectic mix of shops, restaurants, and bars, making it perfect for a leisurely stroll, unique shopping experiences, and sampling exquisite local cuisine.

Next, make your way to the renowned Portland Head Light, one of the most photographed lighthouses in the United States. Located in Fort Williams Park, this historic site offers stunning coastal views, picturesque walking trails, and insightful exhibits about its storied past. It's a must-visit for photography enthusiasts and history buffs alike.

Continue your adventure at the Eastern Promenade, a scenic park providing panoramic views of Casco Bay. With its lush green spaces and recreational facilities, it's an ideal spot for picnicking, walking, or simply soaking in the natural beauty of Portland's waterfront.

Your itinerary wouldn't be complete without a visit to the Maine Narrow Gauge Railroad Museum. This unique museum offers a fascinating glimpse into the history of narrow gauge railroads in Maine. Enjoy a scenic train ride along the waterfront and delve into the historical exhibits that bring this piece of living history to life.

Lastly, step back in time at the Victoria Mansion, an extraordinary example of pre-Civil War architecture and interior design. Marvel at the opulent furnishings, intricate woodwork, and exquisite artwork that adorn this historic landmark, offering an unparalleled glimpse into 19th-century elegance.

This diverse and engaging itinerary will provide a comprehensive experience of Portland's rich history, stunning landscapes, and vibrant local culture.


Recommended Activities

  • Old Port is a historic district featuring cobblestone streets, 19th-century brick buildings, and a vibrant waterfront with shops, restaurants, and bars. It's perfect for a leisurely stroll, unique shopping, and sampling local cuisine.
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  • Trip Point Pin2

    Portland Head Light

    Portland Head Light is one of the most photographed lighthouses in the United States, offering stunning coastal views, historic exhibits, and picturesque walking trails in Fort Williams Park. It's a must-visit for photography enthusiasts and history buffs.
    Open Google Maps Button
  • Trip Point Pin3

    Eastern Promenade

    Eastern Promenade is a scenic park with panoramic views of Casco Bay, lush green spaces, and recreational facilities. It's ideal for picnicking, walking, and enjoying the scenic beauty of Portland's waterfront.
    Open Google Maps Button
  • Trip Point Pin4

    Maine Narrow Gauge Railroad Museum

    The Maine Narrow Gauge Railroad Museum offers a unique glimpse into the history of narrow gauge railroads in Maine. Visitors can enjoy a scenic train ride along the waterfront, explore historical exhibits, and experience a piece of living history.
    Open Google Maps Button
  • Trip Point Pin5

    Victoria Mansion

    Victoria Mansion is an exceptional example of pre-Civil War architecture and interior design. Visitors can marvel at the opulent furnishings, intricate woodwork, and exquisite artwork inside this historic landmark, offering an unparalleled glimpse into 19th-century elegance.
    Open Google Maps Button

Restaurants

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    Duckfat, Portland, ME

    Duckfat, Portland, ME

    Known for its exceptional Belgian-style fries cooked in duck fat, this cozy spot offers a unique and delicious twist on comfort food.
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    Eventide Oyster Co.

    9.2
    $$$$

    Eventide Oyster Co.

    A modern take on the classic oyster bar, Eventide is famous for its fresh local seafood and inventive dishes.
    9.2
    $$$$
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    The Honey Paw

    4.4
    $$$$

    The Honey Paw

    Offering an intriguing mix of Asian-inspired dishes, this restaurant is known for its creative and flavorful menu.
    4.4
    $$$$
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    Boda

    4.5
    $$$$

    Boda

    An upscale Thai restaurant, Boda is celebrated for its authentic street food cuisine and unique cocktail selection.
    4.5
    $$$$
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    Central Provisions - Portland, ME

    Central Provisions - Portland, ME

    This tapas-style eatery features a dynamic menu of small plates made with locally sourced ingredients, making it a must-visit for foodies.
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Stay Recommendations

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    The Press Hotel, Maine

    4.7

    The Press Hotel, Maine

    Housed in the former headquarters of the Portland Press Herald, this hotel offers a unique blend of historic charm and modern luxury, with newspaper-themed decor and artwork.
    4.7
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  • The Francis

    Located in a beautifully restored historic mansion, The Francis offers boutique accommodations with a focus on local art and design, providing a unique and intimate experience.
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    The Danforth Inn

    4.5

    The Danforth Inn

    This elegant inn combines historic charm with modern amenities, featuring beautifully designed rooms, a cozy lounge, and a secret speakeasy bar for a unique stay.
    4.5
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    Blind Tiger Guest House

    4.5

    Blind Tiger Guest House

    Set in a historic townhouse, this guest house offers eclectic decor and a relaxed atmosphere, making it a charming and unconventional lodging choice.
    4.5
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    Inn by the Sea

    Inn by the Sea

    Located just outside of Portland, this eco-friendly luxury resort offers stunning ocean views, beautiful gardens, and a spa, providing a serene and unique escape.
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Local Events & Happenings

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    Lee Brice: What You Know About That Tour 2025

    Lee Brice: What You Know About That Tour 2025

    Please note there is a six (6) ticket limit during the pre-sale and an eight (8) ticket limit during the general on-sale for this event.
    Map IconCross Insurance Arena in Portland (0.83 mi)
    Calendar Icon18 Oct 2025
    Picture for Lee Brice: What You Know About That Tour 2025
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    Maine Mariners vs Reading Royals

    Maine Mariners vs Reading Royals

    The event will take place at Cross Insurance Arena in Portland.
    Map IconCross Insurance Arena in Portland (0.83 mi)
    Calendar Icon19 Oct 2025
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    Maine Mariners vs Wheeling Nailers

    Maine Mariners vs Wheeling Nailers

    The event will take place at Cross Insurance Arena in Portland.
    Map IconCross Insurance Arena in Portland (0.83 mi)
    Calendar Icon25 Oct 2025
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    Maine Mariners vs Adirondack Thunder

    Maine Mariners vs Adirondack Thunder

    The event will take place at Cross Insurance Arena in Portland.
    Map IconCross Insurance Arena in Portland (0.83 mi)
    Calendar Icon1 Nov 2025
    Picture for Maine Mariners vs Adirondack Thunder
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    Maine Mariners vs Worcester Railers

    Maine Mariners vs Worcester Railers

    The event will take place at Cross Insurance Arena in Portland.
    Map IconCross Insurance Arena in Portland (0.83 mi)
    Calendar Icon8 Nov 2025
    Picture for Maine Mariners vs Worcester Railers
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    Dustin Lynch and Scotty McCreery: Two for the Road

    Dustin Lynch and Scotty McCreery: Two for the Road

    There is an 8 ticket limit on this show. This is an all ages show.
    Map IconCross Insurance Arena in Portland (0.83 mi)
    Calendar Icon14 Nov 2025
    Picture for Dustin Lynch and Scotty McCreery: Two for the Road

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