PHOTO: © WATERSTONE PROPERTIES GROUP
Maine’s largest city is gaining attention for both business and leisure as development and revitalization spread through the greater Portland area, which serves roughly half a million people. Set on the scenic shores of Casco Bay, Portland captures a classic New England atmosphere with walkable neighborhoods filled with cozy cafes, chef-driven restaurants and an increasing number of boutique and small luxury hotels. Locals and visitors alike flock to longtime favorites such as Standard Baking Co. on Commercial Street for exceptional bread, Becky’s Diner on the waterfront for a hearty breakfast, and Fore Street Restaurant for locally sourced fine dining. The city’s dining scene has diversified rapidly in recent years, adding everything from Thai and Mexican options to innovative farm-to-table concepts.
Old Port, Portland’s most famous neighborhood, is known for its cobblestone streets and working fishing and lobster boats landing fresh catches daily. This area sparked much of the city’s renaissance and remains central to ongoing revitalization efforts. Newer hotels have brought contemporary comforts to the waterfront: The Canopy by Hilton Portland Waterfront opened in 2021 with 135 guestrooms, multiple meeting rooms and the popular rooftop bar Luna. Also debuting that year, Aloft Portland Downtown Waterfront offers 157 guestrooms and flexible meeting space, while the Cambria Hotel Downtown Old Port opened in 2022 with more than 100 guestrooms and ample meeting facilities.
A short walk from Old Port leads to Congress Street, Portland’s main thoroughfare that stretches nearly six miles through a lively Arts District and the historic West End. The West End showcases well-preserved Victorian and Italianate architecture alongside locally owned restaurants, galleries and shops. The Longfellow, a 48-room boutique hotel that opened in May 2024, blends the neighborhood’s historic character with contemporary luxury, wellness amenities and a strong focus on local art. As the first independent, full-service hotel to open in Portland in more than two decades, the property features a wellness spa, a breakfast and lunch café, and the Five of Clubs bar, inspired by a literary society founded by native son Henry Wadsworth Longfellow. The Longfellow also includes a private meeting room and can accommodate full-property buyouts for group events.
Development continues along Congress Street. Herald Square, a block-long redevelopment on the site of the former Portland Press Herald printing plant, is moving through planning with Phase One set to include a 110-unit condominium tower and a 12-story, 152-room hotel.
Other neighborhoods are experiencing rapid growth as well. West Bayside and East Bayside buzz with rooftop bars, diverse restaurants and food trucks. On the Fore River a few miles southwest of downtown, Thompson’s Point has transformed from an underused parcel into a lively mixed-use campus anchored by the Children’s Museum & Theatre of Maine. Since opening in 2019, Thompson’s Point has added a brewery, concert venue, skating rink, retail and event space, and this spring construction began on a 140-room boutique-style hotel planned for the site.
PHOTO: © WATERSTONE PROPERTIES GROUP
About 15 minutes from downtown in Westbrook, Rock Row occupies a 26-acre former rock quarry and represents Greater Portland’s largest mixed-use development. Still early in its build-out, Rock Row drew more than half a million unique visitors in 2023 and is projected to attract millions more as it expands. Quarryside at Rock Row, which opened in August 2023, is an outdoor gathering spot with a beer garden, live entertainment stage and year-round community programming—able to host private events for up to 1,000 guests. The development is planning a medical and research campus to open in 2025, designed with extensive green space, outdoor infusion hubs and wellness-focused amenities. Future phases will include an innovation hub with Maine’s first large-scale modern convention center and an anchor hotel currently in the initial planning stages.
SCENIC DRIVES
Freeport, less than 30 minutes from Portland, offers coastal views, outdoor activities and shopping that can fill a day. The town is home to the iconic L.L. Bean flagship store and a wide range of outlets and independent boutiques. Freeport’s restaurants highlight fresh-caught seafood and a thriving craft brewery scene, and the area includes more than 3,000 acres of preserved land for hiking, paddling and other outdoor recreation.
About 30 minutes from Portland, the picturesque town of Yarmouth features historic buildings, charming shops and cozy cafés. Local farms and orchards in the area offer seasonal activities like apple picking and fresh-pressed cider.
For a short island escape, the Casco Bay islands are a brief ferry ride from downtown Portland. Visitors can enjoy beachfront lobster bakes, peaceful kayak routes along sheltered shorelines, and relaxed tastings of craft cocktails and mocktails—making the islands an ideal destination for a scenic day trip.