Why Portland, Maine Is the Perfect Memorial Day Getaway: 10 Reasons You’ll Love It
Portland, Maine + Memorial Day Weekend = Your Summer Starter Pack
Memorial Day weekend marks the unofficial start of summer—and if you’re searching for the perfect coastal escape, Greater Portland, Maine should be at the top of your list. Nationally-lauded as a food + drink, arts, and events mecca—this New England gem is in a league all its own. A place where historic charm meets modern innovation and classic coast meets creative culture. Summer never looked (and tasted) so good.
Here are 10 irresistible reasons why Portland, Maine is the perfect Memorial Day weekend getaway—and why you’ll fall in love with it’s beauty and its grit.
COUNTDOWN TOP 10 MUST SEE + DO IN MAINE OVER MEMORIAL DAY WEEKEND
Portland means unmatched meals, a vibrant waterfront, and endless outdoor activities. But, it’s also a portal into Maine’s urban center where you’ll uncover a unique and progressive offering of art + entertainment. Portland offers a little something special for every kind of traveler. Whether you’re bringing the trip out of the group chat for a friends weekend or just bringing yourself for some peaceful solo-travel, you’re be sure to catch a wave—and a vibe.
American flag over Casco Bay, Photo Credits: Digital Edge 
Luna, Photo Credit: Lauren Peters at Visit Portland 
Lobster dinner, Photo Credit: Digital Edge 
Group paddling through Casco Bay; Photo Credit: Digital Edge 
Eating Ice Cream. Photo Provided by Willard Scoops 
Portland’s Working Waterfront Photo Credits: Digital Edge 
Upstairs Deck. Photo Provided by Boone’s Fish House & Oyster Room 
Sailboat passing Fort Gorges., Photo Credit: Digital Edge 
Girl Eating Donut on The Portland Donut Tour. Photo Credit: Good Maine 
Knack Factory Shoot, Photo Credit: Lauren Peters at Visit Portland 
Group boat ride to Portland Head Light; Photo Credit: Digital Edge 
Red Maine Narrow Gauge train; Photo Credit: Maine Narrow Gauge 
Wine Wise Wine Sail; Photo Credit: Lauren Peters at Visit Portland 
Shipyard Gift Shop; Photo Credit: Guided Marketing Services 
Wedding couple kissing and enjoying boat ride; Photo Credit: Kivalo
1 | Explore the Portland Freedom Trail and Discover Maine’s Storied Past
Take a self-guided walk through Portland’s lesser-known but powerful past on the Portland Freedom Trail. This walking route highlights key sites related to the Underground Railroad and the abolitionist movement. For travelers who crave both learning and meaning, this historical experience adds depth to your holiday weekend. Want to take a deeper dive? Join a guided walking tour to take a walk through history with a passionate local expert.
2 | Celebrate Memorial Day Alongside MAiners at the South Portland Parade
The South Portland Memorial Day Parade takes place at Bug Light Park each year and is a great way to get to know locals as this is a fave annual tradition. Festive floats create a touching tribute to America’s heroes. It’s a family-friendly way to kick off your weekend. The parade will go from 9-11am on Memorial Day and feature marching bands, color guards, floats, an array of vehicles. Check out the Events Calendar for more Memorial Day weekend events.
3 | Take in all the coastal views + splendrs of the sea
Nothing says “summer in Maine” like a panoramic ocean view along the rocky coast. Climb to the top of the historic Portland Observatory, the only remaining maritime signal tower of its kind in the U.S. From here, you’ll be rewarded with sweeping views of Casco Bay, downtown Portland, and the surrounding islands. So many sea views, so little time. Now’s the perfect time to explore the sweet treats and renewed summer energy of our area towns.
4 | Live Like a Local at farmer’s markets, parks, and picnics
Start your day with a stroll through Deering Oaks Park, a lush green space filled with old-growth trees and a charming duck pond. Stop by the beloved Portland Farmers’ Market, where you can pick up farm-fresh produce, baked goods, flowers, and handmade crafts. The Eastern Prom has food trucks and easy paddle access from East End Beach if you fancy a dip (after you wait 15 minutes, of course). It’s the perfect place to build your own picnic and relax under the Maine sun.
5 | Catch Live Music at Thompson’s Point
Experience Portland’s vibrant music scene during Memorial Day weekend at Thompson’s Point, a popular waterfront venue hosting exciting concerts and performances, ideal for summer evenings filled with music and camaraderie. Summer Sunsets is a warmer weather classic, a free event with food trucks, live music, and a beer garden on select weekdays to watch the sunset,
6 | Embark on a Casco Bay Harbor Cruise
Kick off the boating season this Memorial Day weekend with a scenic cruise around Casco Bay. Explore stunning lighthouses, picturesque islands, and breathtaking coastline views—a quintessential Portland experience. From tall ships and schooners to motorboat charters and the Casco Bay Lines ferry, you can hop aboard any size vessel.
7 | Wander Through Historic Old Port
Spend your Memorial Day weekend strolling the cobblestone streets of Portland’s historic Old Port district, filled with unique boutiques, inviting cafés, galleries, and waterfront restaurants. It’s the perfect place to shop, dine, and soak in coastal charm. Mark your trip with an iconic Sea Bag made from a repurposed sail. Find the perfect match that will remind you of your Maine memories.
8 | Take a Brewery Tour or join the Maine Beer Trail
Portland is a craft beer lover’s paradise, and Memorial Day weekend is a great time to explore the Maine Beer Trail. Sip your way through award-winning ales, IPAs, and creative seasonal brews. Explore craft brew history by exploring the rich Riverside neighborhood. There you’ll find classics like Geary Brewing Co., holding Maine’s first craft brewing license. Allagash Brewing is an iconic stop in Maine’s beer history that brought Belgian-style brewing to Maine. Foundation Brewing, just across the street, serves-up craft brews and Detroit-style pizza with a cheese wall you won’t soon forget.
9 | Step Into Literary History at the Longfellow House and Garden
For a quiet moment of reflection and a brush with New England’s literary heritage, visit the Wadsworth-Longfellow House, the childhood home of famed poet Henry Wadsworth Longfellow. Tucked behind the Maine Historical Society in downtown Portland, the historic home is beautifully preserved and opens for seasonal tours starting Memorial Day weekend. Don’t miss the adjacent Longfellow Garden, a peaceful urban oasis blooming with spring flowers—a hidden gem right in the heart of the city.
10 | All Aboard the narrow gauge railroad scenic train ride
Bring a bit of nostalgia into your weekend with a ride on the Maine Narrow Gauge Railroad. This charming, historic train runs along the waterfront with gorgeous views of Casco Bay. The ride includes a 40 minute loop around the East End of Portland, starting and ending at the Ocean Gateway. It’s especially fun for families, history buffs, and anyone looking for a relaxing, scenic activity with a touch of classic Maine charm.
Why You’ll Love Memorial Day Weekend in Portland, Maine
From heartfelt moments of remembrance to lobster rolls by the sea, Portland offers the perfect balance of peaceful relaxation and high octane adventure. Whether you’re traveling solo, bringing the whole family, or planning a romantic escape, you’ll find something here that makes you fall in love with Maine’s coast—and keeps you coming back for more. Here’s how you can start planning your trip today.
So pack your bags, grab your sunglasses, and let Portland, Maine welcome you to summer.