The Top 20 Attractions around Wellesley
There are plenty of places to see and visit around Wellesley. Whether you love hiking or cycling, Wellesley is a region where 20
hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.
hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.
Last updated: November 24, 2025
Charles River Greenway
Highlight (Segment) • Cycleway
The Charles River Bike Path, also known as the Charles River Greenway, offers a 22-mile paved route connecting Boston to its western suburbs. Following both shores of the Charles River …
Tip by
Charles River Reservation Bike Path
Highlight (Segment) • Cycleway
The Charles River Reservation stretches 20 miles along the Charles River, offering oppertuity for a range of activities from biking, hiking, and boating to picnics and playgrounds. Open from sunrise …
Tip by
Sign up now to discover places like this
Get recommendations on the best single tracks, peaks, & plenty of other exciting outdoor places.
Sign up for free
Lone Tree Conservation Area
Highlight • Forest
Lone Tree Hill Conservation Land in Belmont, Massachusetts (often called Lone Tree Conservation Area) offers a peaceful mix of forest, meadow, and historic carriage roads. Popular with walkers, runners, and …
Tip by
Jamaica Pond
Highlight • Lake
The lake is beautifully framed by mature trees and even has a boathouse for rowers and sailors. The entire approach to the arboretum is so picturesque that you almost forget you're in the middle of a big city.
Translated by Google •
Tip by
Mass Central Rail Trail: Weston–Wayland Section
Highlight • Cycleway
This section of the Mass Central Rail Trail (MCRT) runs for three miles through Weston, and is part of a planned 25-mile trail stretching from Berlin to Waltham. The trail …
Tip by
Sign up for free to discover even more attractions around Wellesley.
Sign up for free
Already have an account?
Most popular attractions around Wellesley
Get inspired with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures around London and beyond.
Explore more
Still not found the Highlight you’re looking for? See guides of the top attractions in other regions:
Get ready to conquer new peaks
Sign up for Free