Ah, Portland. The sweetest seaside town teeming with tasty restaurants, brimming with breweries, and filled with some of my favorite memories. Earlier this month, I took a quick trip back to the homeland with my boyfriend for a wonderful weekend filled with great food, fun, and some of my favorite people, and it got me thinking that I have never documented all my favorite spots in this cute little city! It’s quaint, it’s walkable, it’s coastal, and it’s all able to be enjoyed within 1.5 hours of Boston. So without further ado, allow me to share what we did to have the perfect short but sweet weekend getaway!
Here’s how to have the best Fall weekend in Portland:
Friday
- Drive up in the afternoon and get settled
- Grab a pre-dinner cocktail at Blyth and Burrows
- Go to Scales for dinner to enjoy some of the best Maine seafood – make sure to grab a reservation early, and don’t sleep on the brown bread to start!
- Head to Lincolns for post-dinner (five dollar) drinks – if you can find it!
Saturday
- Start the day with a scenic stroll along the Eastern Prom
- Grab coffee + a bite from any of the many adorable coffee shops downtown – my personal favorite is Bard Coffee
- Shop downtown along Exchange and Commercial Street
- Eat lunch at Eventide – their brown butter lobster rolls are worth the wait!
- Hit the breweries! There’s a ton to choose from, but my personal favorites are Rising Tide and Après – especially if like me, seltzer is more your thing than beer
- Have a cozy Italian dinner at The Corner Room
- Top off the night with a drink from The Bar of Chocolate – their Salted Caramel Chocolate martini is even better than it sounds!
Sunday
- Start the day with coffee and the best bagel sandwich you’ve ever had at Forage
- Head to Fort Williams State Park for a lovely scenic walk with lighthouse views
- Grab lunch from Duckfat – be prepared to wait in line, but the french fries make it worth it
- Head home!
And that’s it! A quick trip jam-packed with more than enough to eat, drink, and see. And even though these are some of my favorite spots, I by no means mentioned them all! If you’re still hungry, alternate and equally honorable mentions also go to Via Vecchia, The Front Room, Street and Co., Evo, and of course, Flatbread. If you have more time, there’s always fun to be had visiting Freeport to do some shopping and seeing the original L.L. Bean, and of course, if you’re visiting in the summer, there’s more than enough beaches to choose from. It’s a lovely retreat year-round. Enjoy! ☼
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