WEBVTT
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I'm Johnny Mac, and travel is back. Today's episode is
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powered by AI. Hey, we made it to Portland, Maine.
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Step off the bus or out of your car, and
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you're right in a city that looks small on a
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map but feels busy in the best way. There's that
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deep breath of salt air, the gulls calling, and a
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working waterfront where real people are actually working. You can
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see it right away. On Commercial Street, the buildings are
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brick and the pavement's a little bumpy. And down the wharves,
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you'll catch the smell of bait and diesel and fresh fish.
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That's your first clue? You're not in a theme park?
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This is a port that ships and hauls and makes
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a living. Walk it, peek into Custom House Wharf where
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Harbor Fish Market sets out crates of whole fish and
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glistening fillets, and you'll watch somebody wheel a tub of
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lobsters like it's a Tuesday because it is. Start your
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day simple. Grab a coffee at Bard or swing by
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Standard Baking Company for a morning pastry that'll go fast
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if you sleep in. If you want to lean Maine
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right away, get a potato donut from the Holy Donut. Yes,
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they use mashed potatoes, and no, you won't taste anything weird.
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You just get a dense, fresh donut that keeps you
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full when the wind comes off the bay, then keep moving.
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The nicest trick in Portland is you can set your
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own walking tour without trying. Drift toward the ferry terminal.
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Don't buy a ticket yet, just clock where it is.
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You'll want that later. From there, angle east, follow the water,
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and you'll land on a path that swings you away
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from the business of the docks and out to the
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edge of the peninsula. The cobbles and wharves are behind you,
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and it's nothing but Casco Bay, islands on the horizon,
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and that huge sky that can flip from bright to
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fog in five minutes. The famous lighthouse is out there
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in the distance. You'll get your fill of it. Right now,
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just walk, feel the breeze, and watch the working tug
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shoulder by. It's worth climbing a hill before you get
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too settled. Head up to Munjoy Hill. It's a quick,
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honest uphill walk and a good way to understand the city.
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The neighborhood's a mix of old triple-deckers, tidy little yards,
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and a few new places that popped up because everyone
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discovered Portland at the same time. When you pop out
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at the Eastern Promenade, it's one of those views that
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makes you slow down. You've got Casco Bay spread in
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front of you with little green islands dotting the water
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like stepping stones. There's a big grassy slope where you
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can sit, throw down a blanket, and call it lunch.
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The Eastern Prom Trail runs along the edge. You can
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bike it, jog it, or just stroll and bench hop
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if you want your toes in the water. Drop to
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East End Beach. It's sandy enough to sit and skim stones,
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and it's calm. If you're the type who wants to
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get on the water, look for Portland Paddle by the
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beach in season. They'll set you up with a kayak
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or a paddleboard for an hour, and you can hug
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the shoreline or thread out toward the islands if conditions
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are right. It's not extreme. It's just a great way
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to stare at the city from the water and hear
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only your own paddle drip. Behind you, that funny little
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old rail line you crossed, that's the narrow gauge track.
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When they're running, you can ride a short train down
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the water's edge with kids grinning out the windows like
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it's 1910 again. If you like a climb and a view,
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the Portland Observatory sits up on Congress Street. It's the
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historic Maritime Signal Tower, and when it's open for tours,
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you can go up, get a look that's almost 360,
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and hear how captains once used it like a neighborly
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text chain. It's an easy way to make the city
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feel small and know how it all fits. Now drop
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back down the hill and point yourself at Washington Avenue
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and East Bayside. It used to be warehouses and garages
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with not much going on, and now it's where you
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go when you want an easy night that builds on
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its own. Start simple with a snack. Duck Fat's Fritz
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Shack sits here in season, and you can grab a
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cone of those twice-fried fries with a side of mayo
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you don't have to explain to anyone. Take them into
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the Oxbow Blending and Bottling Courtyard across the way, sit
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at a picnic table under bulb lights, and watch a
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half-dozen different conversations unfold around you. It's the kind of
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place where everyone's relaxed because they didn't have to dress
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up or fight a reservation system to get in. Turn
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a corner and you get oysters. The Shop by Island
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Creek lines them up on ice from all over the
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Maine coast. The trick here is to go mid-afternoon or
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early evening and just order a half-dozen with a squeeze
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of lemon and a beer. Oysters on the half-shell that
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taste like the cleanest seawater you ever had? That's your move.
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If you want a proper sit-down dinner, Izakaya Monado is
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small and friendly, and the plates are made to share.
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Don't overthink it. They'll walk you through the menu. Or
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go a little farther down to Terlingua if you feel
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like barbecue with some Tex-Mex heart and a cocktail that
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isn't sweet. The point of this neighborhood is you can
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float place to place, snack to snack. If beer's your thing,
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Rising Tide and Good Fire are right here. You can
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sip something hoppy, something malty, or ask for whatever's easy
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drinking and not 8%. If beer isn't your thing, the
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Urban Farm Fermentory does ciders, kombucha, and meads. Tasting a
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flight of four small pours of fermented tea doesn't sound
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like a night out until you do it. Then it
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absolutely does. The whole area is walkable, lit with string lights,
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and kind of perfect for evenings when you're not trying
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to chase down a famous place, just trying to have
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a good time and talk. Park once if you drove,
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or don't drive at all. Either way, you'll be glad
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you didn't lock yourself into one reservation across town and
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miss the serendipity of just wandering into what looks good.
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People talk about Portland as a food town, but it's
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also an easy art town. Give yourself a Congress Street afternoon.
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Start at Monument Square. It's that brick plaza in front
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of the big library with a monument in the middle
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and pigeons holding union meetings. There are used book carts
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some days and Longfellow Books just off the square is
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the kind of indie bookstore you duck into just for
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a second and walk out with something you'll read cover
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to cover on the ferry. Portland's Museum Row is right there, too.
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The Portland Museum of Art doesn't swallow your day, which
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I like. You can spend an hour or two, see
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work by Maine's painters and a few big names rolled through,
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and then you're back outside. If you land here the
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first Friday of the month, the galleries and studios on
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and off Congress open up in the evening. It's First
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Friday Art Walk. You just walk, poke into spaces, chat
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with artists, and maybe buy a small print that'll make
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you smile every time you look up over your desk.
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Keep walking up to Longfellow Square. It's named after Henry
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Wadsworth Longfellow, whose house sits a bit down the hill
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on Congress. The house shows up on city tour maps,
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but even if you don't go inside, the statue and
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the square give you a sense that, yep, real writers
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planted roots here way before social media. If you need
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a coffee, Tandem Coffee Plus Bakery in that old gas
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station building pours a mean cup and hands you a
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biscuit that flakes onto your shirt. That's how you know
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it's right. Around you, Mech A & D students are
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hauling portfolios and sketchbooks in the State Theater marquee. is
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throwing you bands you've definitely heard of. If you're in
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town on a show night and tickets are left, it's
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a great venue to see somebody you like without needing binoculars,
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slide over to Deering Oaks Park if it's a farmer's
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market day. In season, vendors line the paths with greens, bread, cheese,
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and berries, and you can buy your lunch right there
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and go sit by the duck pond. City life, but
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at about six miles per hour. At some point, that
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ferry you clocked earlier will start calling your name. Do
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a half day on Peaks Island. It's easy. Head to
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the Casco Bay Lines Terminal, Rates change, but it's pocket
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money compared to a tour boat. Check the board, pick
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a departure, and line up a little early if you
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want to sit outside. The crossing takes 20 minutes if
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you're not on a milk run. Sit on the open
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deck and watch the city slide away and the island
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step forward like you're walking through a beaded curtain. When
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you land, you've got a few choices. There are places
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by the dock that'll rent you bikes or a golf cart.
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If you're not up for pedaling, the golf cart is
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silly in the best way. If you are, that four-mile
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loop road is exactly the right size to feel like
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an adventure without feeling like a workout. Roll clockwise, the
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island changes as you go. Out by the south side,
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you'll find Sandy Beach tucked down a path. It's small,
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and you guessed it, sandy. People set up low-key, and
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the water will wake your feet up even in August.
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If you like a little history, fold it into your walk.
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Head inland to Battery Steel, a World War II-era fort
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mostly reclaimed by nature. Bring a flashlight or use your phone.
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You'll walk through old concrete corridors that swallow sound, then
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pop out on top with a view back over the
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trees to the water. On your loopback, stop at the
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little market near the ferry for an ice cream or
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a cold drink and sit on the seawall. There's really
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nothing you have to do here. You just slow down,
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make sure you know the return schedule. Boats run often enough,
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but it's nice to time it so you're heading back
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around golden hour with the city lighting up in front
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of you. On the return, the wind ramps up a notch.
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Zip your jacket. You'll wish you had one if you don't.
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If you've got a car or you like a longer walk,
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cross the Casco Bay Bridge to South Portland and take
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the Greenbelt Walkway. South Portland's not a suburb in the
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boring sense. It's more neighborhoods strung along the water with
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big views back to Portland. Bug Light Park sits on
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a point with a tiny white lighthouse at the end
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of a short walkway. It looks like a dollhouse compared
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to the famous one up the coast, but the look
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back across the harbor at the skyline is one of
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the best angles you can get. Keep going to Spring
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Point Ledge Light, where a big granite breakwater lets you
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walk out over the water itself. Step carefully. The gaps
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are real, and if the wind's up, you'll get a
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little spray. Right there, the stone walls and grass of
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Fort Preeble are half-hidden under the hill. It's an old fort,
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a little tumbled, but you can trace the edges with
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your eyes and picture the harbor guarded by cannons, then
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now by people walking dogs. Willard Beach sits right around
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the bend. It's a friendly neighborhood beach where dogs run
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at certain hours and families plop down with snacks, and
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it's not a scene. If you didn't eat on the
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Portland side, Scratch Baking Co. 's in Willard Square makes
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bagels that crunch outside and chew inside, and the smell
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will pull you in from half a block. They sell out.
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That's not a threat, it's just motivation to show up
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before noon. When you're done with all that walking, Red's
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Dairy Freeze on Cottage Road is a perfect soft-serve stop.
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It's the kind of place where the menu is basically
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your childhood. You get a cone, you stand in the
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lot with everyone else, and you're happy. If you loop
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back along the Greenbelt, give yourself a second at a
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bench to watch the freighters come and go. It's not complicated,
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it's just a good day. There's another cluster of good
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stuff out at Thompson's Point where an old rail yard
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sits by the Four River and somehow turned into a
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place locals actually use. If you've got kids in tow
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or you enjoy interactive spaces that aren't boring, even if
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you don't. The Children's Museum and Theater of Maine lives
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here now. It's bright and smart and hands-on. Outside, picnic
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tables spread out on the grass and food trucks show
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up when the weather's playing along. Bissell Brothers Brewery anchors
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one end with a big lively tasting room. You can
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grab a table. Sip something you like and look out
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at a strip of boardwalk and marsh that glows at sunset.
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Stroudwater Distillery is a few doors down if you're a
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whiskey person. In summer, they set up a stage and
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throw outdoor concerts that sell out but always look like
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the best backyard party in town. In winter, there's an
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ice rink that somehow turns this old industrial slice into
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a snow globe. If you're the sort who loves seeing
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where the beer stars came from, take a ride out
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to the industrial waste scene near where Allagash set up shop.
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It's basically a row of low buildings and parking lots
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that birthed a handful of breweries that punched above their weight.
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Allagash does tastings and tours you can often book in advance.
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The taproom's got a patio, and the servers actually seem
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happy to talk about what you're tasting without a lecture. Money-wise,
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you don't need to eat a tasting menu to taste Portland.
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Coffee and bakery in the morning, chowder and a sandwich
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for lunch, and one or two small plates for dinner
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gets you the spirit. Tip your servers, be patient with lines.
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The city runs on hospitality, and the pace is calm
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even when the sidewalks aren't. Bring comfortable shoes, bring a
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light pack, bring curiosity. Portland isn't here to impress you
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with one big thing. It's here to stack good, small,
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easy moments until you look around and realize, huh, this