Your Guide To a Weekend in Portland

Summer is right around the corner and with warmer temps and longer days on the horizon, it might be time to start thinking about booking a few weekends away. With weddings and graduations dotting your calendar, you and your friends might be looking to take a trip of some kind. Whether it’s celebrating a bride to be, a recent grad, a reunion, or just some time away with your nearest and dearest -- look no further than Portland, Maine!


Portland is the largest city in Maine, located about an hour North of the New Hampshire border and about an hour and a half from the Boston area. You can easily get to Portland by car, train, or air. Once here, the city is full of history, foodie hotspots, fun breweries, picturesque coastal scenes, outdoor activities, and a perfectly-sized pocket of nightlife. A long weekend itinerary in Portland is easily filled with great restaurants and bars, breathtaking views, and quintessential New England charm that will be the perfect backdrop to your ultimate trip! 


Where To Stay: 

  • Portland Press Hotel, Autograph Collection: a luxury option in downtown Portland, offering chic accommodations and a gourmet restaurant. 

  • The Francis: locally owned, boutique hotel in the historic West End neighborhood with a spa!

  • Best Bower: in the hip East End of Portland on Munjoy Hill, a guesthouse with 6 rooms in a renovated, historic building! 

  • Air BnB: there are so many wonderful options for short-term rentals in Portland, offering an authentic home-away-from-home during your stay! 


Where To Eat and Drink:

  • Four Points Marina: waterside bar with a food truck and delicious frozen drinks! 

  • Eventide: arguably one of the best lobster rolls in the city! Pro Tip- get there early to put your name in as wait times in the summer can be long… don’t worry though, it’s worth it! 

  • Chaval:  a busy bistro in the heart of the West End with James Beard nominated chefs. 

  • One of the many breweries! 

  • Luna:  rooftop bar on the waterfront!

  • LB Kitchen:  at the foot of Munjoy Hill, LB Kitchen is a great option for a fresh, healthy meal on the go! 

  • Blake Orchard:  our downstairs neighbors! Blake Orchard is known for fresh juices and smoothies and delicious coffee. Pro Tip- grab a smoothie bowl after your morning spin class at Rêve!


What To Do: 

  • Explore the waterfront and Old Port — there are countless restaurants, bars, and local shops along the waterfront and in the historic Old Port. Get lost wandering through the cobblestone streets! 

  • Stroll on the Eastern Promenade —  the Eastern Promenade offers breathtaking views of Casco Bay and a refreshing breeze. Stroll along the prom or bring a blanket and settle in. Pro Tip: Food Trucks line up here in the summer, so it’s a great spot for a casual meal!

  • Find a lighthouse — head over the bridge to South Portland or Cape Elizabeth to spy some of the most photographed lighthouses in the world, right here in Portland! 

  • Catch a show at Thompson’s Point -- a fun outdoor venue for concerts, outdoor movies, food trucks and more! 

  • Take a class at Rêve — we’d love to see you and your group for a spin or mat class during your visit to Portland! For group rates and pre-booking options, send an email to info@revecyclingstudio.com for more details.

We believe wholeheartedly in celebrating the larger Portland community that makes this little city so special. We hope to catch you and your crew up here in Vacation Land sometime this summer to experience the magic. Oh — and don’t forget! Reach out and let us know that you’re coming to class! Give us a follow on social media for studio information and more recommendations on local spots. We’ll help make your weekend here in town special and make sure you hit all of the town’s highlights!


Stephanie Cabot