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Mountain Club on Loon

The Adventurer's Itinerary

From memorable city kayak runs to hard core climbing New England offers endless ways to keep you moving - and exploring -  all year long. 

Day

1
Biking the Cape Cod Rail Trail
MA Office of Tourism

Chatham, Massachusetts

Beach
Dining
Museum

Six Cape towns and several National Seashore beaches are part of the itinerary of the 22-mile paved Cape Cod Rail Trail. 

EAT

Chatham Pier Fish Market

The chowder is divine but it’s the setting that will keep you coming back for seconds. 

PLAY

AWSC Chatham Shark Center

You’re going to need an extra hour at this lively museum and educational center, which puts its  focus on great white sharks.  

STAY

Greyfinch Chatham Inn

Modern amenities meet coastal charm at this 30-room Cape retreat. 



Chatham Bars Inn

Get the full Cape experience (water views, delectable seafood, golf and spa treatments) without leaving the grounds. 

 

Day

2
Boats sailing on the water with a bridge in the background
Discover New England

Mystic, Connecticut

Lighthouse
Museum
Sailboat

Mystic’s rich maritime history comes alive as you trim your sails and explore the area’s coastal beauty, nearby islands, and captivating lighthouses.

EAT

Oyster Club

To-die-for oysters, pasture-raised beef and arguably the finest lobster roll in town are all served up at this seafood-focused favorite. 

PLAY

Mystic Seaport Museum

The nation's leading maritime museum gives visitors an up-close view at four National Historic Landmark vessels as well as a working preservation yard.  

STAY

Steamboat Inn

Mystic’s only on-the-water hotel is also centrally located. 



Hilton Mystic

Business travelers and families have a home at this property, which is within easy walking distance to the famous aquarium. 

Day

3
Person in red shirt rock climbing steep rock face
NH Office of Tourism

Providence, Rhode Island

Cafe
City
Rock Climbing

Lincoln Woods State Park caters to rock climbers of all abilities and offers the chance to test your skills year-round. 

EAT

PVDonuts

The lines start early at this famed bakery, where its gorgeous donuts are almost as beautiful to look at as they are to eat. Almost.

PLAY

East Bay Bike Path

Keep the action rolling on this scenic 15-mile trek between Providence and Bristol.  

STAY

The Beatrice

Treat yourself to the luxury you deserve at this centrally-located hotel. 



Newport Harbor Island Resort

Beautiful water views and exquisite service help define this hotel, located on an island just off its namesake city. 

 

Day

4
two people sea kayaking

Boston Harbor Islands National and State Park, Massachusetts

Cafe
City
Kayak

Eastern Massachusetts’ largest recreational open space spans 33 islands and peninsulas, giving sea kayakers a number of delightful landing spots.

EAT

High Street Place

Blackbird Doughnuts, Hayley Jane’s Fried Chicken, Gracenote Coffee and Mamaleh’s Deli all make their address at this acclaimed food hall. 

PLAY

View Boston at Prudential Center

Keep on moving to the 52nd floor of the Pru, where Boston’s cityscape comes into complete focus. 

STAY

XV Beacon

Luxury touches abound at this hotel, which resides in a turn-of-the-century Beaux-Arts building in Boston’s historic Beacon Hill. 



The Revolution Hotel

Stylish value is at the heart of this boutiquey South End favorite. 

 

Here's Your Route

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