Portland, Connecticut is a hidden gem in Middlesex County. This charming town offers a perfect blend of outdoor adventures and small-town charm.
Portland’s riverfront location makes it an ideal spot for water activities, hiking, and scenic views.
You’ll find plenty to do in Portland. Brownstone Adventure Sports Park offers thrilling zip lines and water sports.
Golf enthusiasts can enjoy three courses in town. For a more relaxed experience, visit a local winery or take a kayak out on the lake.
Nature lovers will appreciate the hiking trails in the state forest. Music fans can attend riverfront concerts.
With its mix of outdoor activities and small-town atmosphere, Portland is a great destination for your next Connecticut getaway.
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How To Get To Portland
Getting to Portland, Connecticut is easy. You have several options to reach this charming town.
By car, Portland is about a 2-hour drive from New York City. Take I-95 North, then merge onto CT-9 North.
If you prefer public transportation, trains and buses run from major cities to nearby Hartford. From there, you can take a short taxi ride to Portland.
Flying is another option. The closest airport is Bradley International Airport, about 30 minutes away. You can rent a car at the airport for the drive to Portland.
Once in town, walking is a great way to explore. Portland’s compact size makes it perfect for strolling and taking in the sights.
For day trips, consider renting a bike or using local bus services. These options let you see more of the area at your own pace.
What To See In Portland
Portland, Connecticut offers a variety of attractions for visitors. You can start your trip by exploring the scenic Connecticut River. The river provides great spots for fishing and boating.
For outdoor enthusiasts, the Air Line Trail is a must-visit. This rail trail offers miles of hiking and biking opportunities through beautiful forests and meadows.
Don’t miss the chance to visit a local vineyard. Portland’s wineries offer tours and tastings, giving you a taste of Connecticut’s wine culture.
If you’re traveling with kids, head to the Riverfront Park. It’s perfect for picnics and has a playground for children to enjoy.
Golf lovers will find several courses in the area. You can practice your swing while taking in the scenic views of the brownstone hills.
For a unique experience, visit during the Portland Agricultural Fair. This annual event showcases local produce, livestock, and entertainment.
Remember to explore the charming downtown area. You’ll find local shops and restaurants that capture the town’s friendly atmosphere.
Where to Stay in Portland
If you know when you are planning to go but haven’t decided on accommodation, then use the map below to get an idea of which properties are available and to compare prices during the period you wish to travel.
Enter your proposed dates and use the ‘+’ to zoom in on a location and reveal more properties. Click on the price above a property to see more information.
(Please note that this selection will also include some vacation homes, AirBnBs, and VRBOs for those who are interested in that form of accommodation!)
History of Portland
Portland, Connecticut has a rich past dating back thousands of years. Native Americans called Wangunk lived in the area 8,000 to 10,000 years ago. They hunted local animals and grew crops along the Connecticut River.
European settlers arrived in the 1600s. The town was originally part of Middletown. It went through several name changes:
- East Middletown
- Conway
- Chatham
Portland was officially incorporated as a town in 1841. The name comes from Portland, England, famous for its stone quarries.
Two industries shaped Portland’s early growth:
- Shipbuilding along the Connecticut River
- Brownstone quarrying
Portland brownstone became world-famous. You can still see it in buildings across the Northeast. The stone industry boomed in the 1800s, employing many immigrants.
Today, Portland blends its historic charm with modern amenities. You can explore local history at the Portland Historical Society. They offer exhibits, programs, and even mark historic sites around town.
Towns Near Portland
Portland, Connecticut is surrounded by charming towns worth exploring. You’ll find a mix of historic charm and modern attractions in these nearby destinations.
Old Lyme, just a short drive away, offers beautiful beaches and a rich artistic heritage.
You can stroll through its quaint downtown, visit art galleries, or relax on the shore.
Middletown, located north of Portland, is home to Wesleyan University. You’ll enjoy its vibrant Main Street, filled with shops and restaurants.
The city also boasts beautiful parks along the Connecticut River.
East Hampton, known as “Belltown” due to its bell-making history, provides a glimpse into Connecticut’s industrial past. You can visit the Air Line Trail for hiking or biking.
Glastonbury, to the north, combines rural charm with modern amenities. You’ll find pick-your-own farms, historic sites, and excellent dining options.
Cromwell, just northwest of Portland, hosts the Travelers Championship golf tournament yearly. You can enjoy its parks or visit local wineries.
These towns offer unique experiences within easy reach of Portland. Whether you’re interested in history, outdoor activities, or local culture, you’ll find plenty to explore in the area.
Get a discount of 15% to 70% on accommodation in Middlesex County! Look for deals here:
Middlesex County Hotels, Apartments, B&Bs
