Harpswell, Maine, is one of those coastal destinations that feels a little different from the busier towns farther south. With narrow peninsulas, rocky shorelines, quiet coves, and small islands connected by bridges, it’s a wonderful place to explore a less crowded side of the Maine coast.
Located just south of Brunswick, Harpswell includes several peninsulas and islands, including Bailey Island and Orr’s Island. It’s an easy destination for a day trip from Portland or Freeport, but there’s enough here to fill a relaxed weekend.
We recently spent a day exploring Harpswell and Bailey Island, hiking the beautiful Cliff Trail, walking along the dramatic shoreline at Giant’s Stairs, and stopping at Land’s End and the historic Cribstone Bridge.
Whether you’re looking for a coastal hike, scenic ocean views, a seafood lunch, or simply a beautiful place to spend the afternoon, here are the best things to do in Harpswell and Bailey Island, Maine.
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Quick Guide to Visiting Harpswell & Bailey Island
| Location | Midcoast Maine, south of Brunswick |
| Best for | Coastal hiking, ocean views, photography, quiet exploring |
| Time needed | Half day to a full day; longer for a relaxed weekend |
| Best time to visit | Late spring through fall |
| Getting around | A car is recommended |
| Nearby destinations | Brunswick, Freeport, Portland |
| Our favorite stops | Cliff Trail and Giant’s Stairs |
Best Things to Do in Harpswell & Bailey Island
1. Hike the Harpswell Cliff Trail
Our favorite hike in the Harpswell area was the Cliff Trail. This 2.2 mile loop takes you along several bodies of water and climbs to a small cliff for incredible views. Parts of the trail have a wide and easy walking trail and the cliff side is slight more challenging with roots
If you’re comfortable walking over roots, rocks, and irregular terrain, it’s worth continuing farther along the trail. The scenery is gorgeous, and the variety makes this one of the most rewarding outdoor adventures in Harpswell.
In addition to the views, the trail also has a ferry building area and when we were there a children’s book walk through the forest.
2. Walk the Giant’s Stairs Trail on Bailey Island
If you only have time for one coastal walk on Bailey Island, Giant’s Stairs should be high on your list. This is a short walk right on the rocky coastline, but the rocks here are unique.
This scenic shoreline trail offers spectacular ocean views and some of the most interesting rock formations we saw during our visit. The coastline here is rugged and dramatic, with waves breaking against the rocks and distinctive geological features along the shore.
We especially loved the contrast between this walk and Cliff Trail. While Cliff Trail offers a wooded hiking experience, Giant’s Stairs puts you right along the rocky Maine coastline.
It’s also a wonderful place for photography, particularly if you enjoy dramatic coastal landscapes.
3. Visit Land’s End on Bailey Island
At the southern end of Bailey Island, Land’s End is a scenic stop with expansive views across the water.
We stopped here during our exploration of the island, and it’s a natural addition to a day that includes Giant’s Stairs.
The views are the main attraction. It’s a good place to enjoy the coastal scenery, take photographs, and appreciate how far the narrow island stretches into Casco Bay.
Allow a little time to explore rather than simply driving to the end of the road and turning around.
4. See the Historic Bailey Island Bridge
The Bailey Island Bridge, also known as the Cribstone Bridge, connects Orr’s Island and Bailey Island.
Unlike a typical bridge, its distinctive construction uses stacked granite cribwork allowing the rides to flow through the bridge. It’s one of the area’s most recognizable landmarks and an interesting stop for anyone who enjoys coastal history or photography.
We stopped to see the bridge while exploring Bailey Island, and it’s worth taking a moment to appreciate its unusual design rather than simply driving across it.
5. Explore Stover’s Point Preserve
Stover’s Point Preserve is another place to consider if you’re looking for coastal scenery in Harpswell. The preserve is known for its shoreline setting and opportunities to enjoy the quieter side of the Maine coast.
It’s a good alternative for visitors who prefer exploring the shoreline rather than taking a longer hike.
6. Visit Potts Point Preserve
Potts Point Preserve is another scenic destination worth considering, especially for visitors interested in shoreline exploration and coastal wildlife.
Because this is a coastal preserve, visitors should pay attention to tides, shoreline conditions, and any posted access restrictions.
7. Spend Time at Mitchell Field
Mitchell Field is a public waterfront property in Harpswell with open space and views toward the water.
It’s a different experience from the rocky coastal walks and forest trails, making it a useful option for visitors who want a relaxed stop or a place to spend some time outdoors.
8. Explore Harpswell by Kayak
With its protected coves, islands, and long shoreline, Harpswell is an appealing destination for paddling.
Kayaking can offer a completely different perspective on the coastline, particularly around quieter coves and sheltered stretches of water.
If you’re planning to paddle, choose a route appropriate for your experience and check the tides, wind, currents, and marine forecast. Guided outings may be a better choice for visitors unfamiliar with the area.
9. Take a Boat Tour Around Casco Bay
A boat tour is another way to appreciate Harpswell’s island geography and working waterfronts.
Depending on the available excursions, visitors may find sightseeing cruises, wildlife-focused trips, or other opportunities to explore the islands from the water.
10. Enjoy Fresh Maine Seafood
A visit to Harpswell or Bailey Island is also an opportunity to enjoy the local seafood scene.
A casual waterfront lunch can fit naturally between the hiking and sightseeing stops, particularly during the warmer months.
Some restaurants operate seasonally, so it’s worth checking opening dates and hours before planning your day around a particular location.
Best Hikes and Coastal Walks in Harpswell
For visitors who primarily want to spend time outdoors, I’d prioritize these walks:
| Trail or destination | Best for | |
|---|---|---|
| Cliff Trail | Woodland hiking and cliff views | Visited |
| Giant’s Stairs | Dramatic rocky shoreline | Visited |
| Stover’s Point Preserve | Relaxed coastal exploration | Not yet visited |
| Potts Point Preserve | Shoreline scenery and wildlife | Not yet visited |
Our recommendation: If you have time for two outdoor stops, combine Cliff Trail and Giant’s Stairs. They offer very different experiences and are both highlights of the area.
One-Day Harpswell & Bailey Island Itinerary
You can see several of Harpswell’s highlights in a single day, especially if you enjoy combining short hikes with scenic drives.
Here’s a suggested route based on the places we explored.
Morning: Hike Cliff Trail
Start with Cliff Trail while you have plenty of energy and time to enjoy the hike.
Choose the easier section or continue toward the cliff if you’re comfortable with the more uneven terrain.
Allow enough time for photographs and a relaxed pace.
Late Morning: Drive Toward Bailey Island
Continue south through Harpswell toward Orr’s Island and Bailey Island.
As you cross the Cribstone Bridge, take time to appreciate its unusual granite construction. Stop only where parking and pedestrian access are permitted.
Midday: Lunch on Bailey Island
Plan a casual seafood lunch or bring a picnic, depending on the season.
Early Afternoon: Giant’s Stairs
Spend time walking along the rocky coastline at Giant’s Stairs.
This is one of the most scenic stops of the day, so don’t rush it. Bring your camera and enjoy the views.
Late Afternoon: Land’s End
Continue toward the southern end of Bailey Island and finish your exploration at Land’s End.
It’s a beautiful final stop before heading back toward Brunswick, Freeport, or Portland.
Have more time? Consider adding another coastal preserve, a kayaking excursion, or a longer seafood stop.
Where to Eat in Harpswell & Bailey Island
Harpswell and Bailey Island have several options for enjoying Maine’s coastal food traditions, especially during the warmer months.
For a day trip, I’d look for a casual seafood restaurant or waterfront spot that fits naturally into your route.
Where to Stay in Harpswell & Bailey Island
Although Harpswell works well as a day trip, staying overnight gives you more time to explore the coastline at a slower pace.
Consider these types of accommodations:
- Waterfront inns and cottages: Ideal for a relaxed coastal getaway.
- Vacation rentals: Useful for families or visitors staying several nights.
- Brunswick accommodations: A convenient base for exploring Harpswell and nearby Midcoast destinations.
- Freeport accommodations: Another option if you’re combining coastal exploring with shopping and other attractions.
Best Time to Visit Harpswell & Bailey Island
Spring
Spring can be a peaceful time to explore the coastline before the busiest summer travel period. Be prepared for variable weather and muddy trail conditions.
Summer
Summer is a popular season for coastal activities, boating, kayaking, and waterfront dining. Expect more visitors at well-known scenic stops.
Fall
Fall is a wonderful season for hiking and scenic drives. We visited during autumn and enjoyed combining woodland trails with dramatic coastal scenery.
Be aware that some restaurants and tourism businesses reduce their hours or close seasonally.
Winter
Winter offers a quieter coastal experience, but visitors should plan for cold temperatures, ice, wind, and limited seasonal services.
Getting to Harpswell & Bailey Island
Harpswell is located south of Brunswick, Maine, and is best explored by car.
It’s a convenient addition to a trip that includes Portland, Freeport, or other Midcoast Maine destinations.
Because the town includes multiple peninsulas and islands, destinations that appear close together on a map can require additional driving time.
Rather than trying to visit everything, choose a few stops that fit your interests and allow time to enjoy them.
Practical Tips for Visiting Harpswell
- Bring sturdy footwear. Even short coastal walks can include roots, rocks, and uneven ground.
- Check the weather. Exposed shoreline locations can be windy and conditions can change quickly.
- Respect coastal access. Follow signs, observe private-property boundaries, and park only in designated areas.
- Check the tides. This is especially important when exploring shoreline preserves or planning paddling activities.
- Bring water and snacks. Services are spread out, and some businesses are seasonal.
- Don’t rush. Harpswell is best enjoyed with time to stop, walk, and appreciate the scenery.
Frequently Asked Questions About Harpswell, Maine
Is Harpswell, Maine, worth visiting?
Yes, especially if you enjoy scenic coastal drives, hiking, rocky shorelines, and smaller Maine communities. Harpswell offers a different experience from busier coastal tourist destinations.
Can you visit Harpswell and Bailey Island in one day?
Absolutely. A full day gives you time for a hike, a coastal walk, several scenic stops, and a relaxed lunch.
What are the best hikes in Harpswell?
Cliff Trail and Giant’s Stairs are two excellent choices. Cliff Trail offers a woodland hike with more uneven terrain toward the cliff, while Giant’s Stairs is particularly memorable for its rocky coastline and ocean views.
Is Bailey Island part of Harpswell?
Yes. Bailey Island is one of the islands that make up the town of Harpswell.
Do you need a car to visit Harpswell?
A car is the most practical way to explore the area’s spread-out peninsulas, islands, trailheads, and scenic stops.
Explore More of Maine
Harpswell is just one of many beautiful places to explore along the Maine coast.
If you’re planning a longer trip, consider combining it with Brunswick, Freeport, Portland, or other Midcoast destinations.
Explore our Maine Travel Guide for more ideas for outdoor adventures, coastal towns, and weekend getaways.
Author: gstuppy
Gretchen is a New Hampshire-based travel writer, outdoor adventurer, and founder of New England Uncovered. With over 20 years of experience in outdoor education and a passion for exploring off-the-beaten-path destinations, she shares firsthand guides to New England's best hikes, hidden gems, and outdoor adventures. When she's not writing, you'll find her hiking, paddling, or exploring somewhere new with her family.
