The Massachusetts Bucket List
Massachusetts is filled with old history, seafood, and lots of seaside towns! It’s worth exploring for a long weekend, if not, doing the whole state in a week.
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Boston
Kind of Visit: City, Historical - If you’re a food and/or an art-lover, this is the perfect city for a weekend!
Where to stay
Fairmont Copley Plaza - Visit the Merry-go-round bar, which was an actual Merry-go-round!
The Lenox Hotel - Built in 1900 - Judy Garland lived there in 1968 (you can now rent her suite)!
where to dine & drink
Caffe Vittoria - The oldest Italian cafe in Boston.
Carrie Nation Cocktail Club (Speakeasy)
Modern Pastry - Speakeasy in the basement called “Modern Underground”.
The Baldwin & Sons Trading Co. - A speakeasy on the second floor of The Baldwin Mansion.
Union Oyster House - It is nearly 200 years old!
Things to see & do
Bodega - You’ll only find it if you travel to a rundown convenience store in the Back Bay, and you’ll have to push aside a specific Snapple vending machine to get inside. It’s a luxury shopping brand that celebs frequent.
Boston Public Library - Completed in 1895, it houses over 19 million volumes and electronic resources.
Brattle Book Shop - Open since 1825.
Great Molasses Flood Plaque - Picture a two-storey wave of molasses moving at 35 MPH.
Mount Auburn Cemetery - Paul Revere, Samuel Adams, Mary Baker Eddy and even Mother Goose are buried there!
Museum of Science - Houses the World's Largest Air-Insulated Van de Graaff Generator.
Schoolmaster Hill - Ralph Waldo Emerson lived there for 2 years.
Cape Cod
Cape Cod is a series of connected towns that are within minutes of each other. All places will be labeled with where they are located (Martha’s Vineyard and Nantucket are in their own section).
Kind of Visit: Historical, beach vacation - One of the best trips to learn about the very first settlers in the United States!
WHERE to stay
A Little Inn on Pleasant Bay (Orleans) - Top-rated!
A Provincetown Hotel (Provincetown)
An English Garden Bed & Breakfast (Dennis Port)
AWOL (Provincetown)
Beacon Light Guesthouse (Provincetown)
Cape Colony Inn (Provincetown)
Carpe Diem Guesthouse & Spa (Provincetown)
Eben House (Provincetown)
Inn on the Sound at Falmouth (Falmouth)
Land's End Inn (Provincetown)
Pleasant Bay Village Resort (Chatham)
Salt House Inn (Provincetown)
The Platinum Pebble Boutique Inn (West Harwich)
Wequassett Resort and Golf Club (Harwich)
White Porch Inn Art Hotel (Provincetown)
where to dine & drink
Snowy Owl Coffee Roasters (Brewster)
Spinnaker Restaurant (Brewster)
Scargo Cafe (Dennis)
The Pheasant (Dennis)
The Ocean House Restaurant (Dennis Port)
Hole In One Bakery & Coffee Shop (Eastham)
C Salt Wine Bar & Grille (Falmouth)
Maison Villatte (Falmouth)
Pickle Jar Kitchen (Falmouth)
The Glass Onion (Falmouth)
Buca's Tuscan Roadhouse (Harwich)
Twenty-eight (Harwich)
Alberto’s Ristorante (Hyannis)
Brazilian Grill (Hyannis)
Naked Oyster (Hyannis)
Spoon & Seed (Hyannis) - Open for breakfast and lunch only
Bleu (Mashpee)
The Beacon Room (Orleans)
Lobster Pot (Provincetown)
The Canteen (Provincetown)
The Mews Restaurant & Cafe (Provincetown)
Belfry Inn and Bistro (Sandwich)
Red Cottage Restaurant (South Dennis)
PB Boulangerie Bistro (South Wellfleet)
Gerardi’s Cafe (South Yarmouth)
Bookstore & Restaurant (Wellfleet)
CERALDI (Wellfleet)
Kream n Kone (West Dennis)
Ann and Fran’s Kitchen (West Yarmouth)
Keltic Kitchen (West Yarmouth)
Old Yarmouth Inn (Yarmouth Port)
Things to see & do
Crosby Mansion (Brewster)
Chatham Orpheum Theatre (Chatham) - Opened in 1915.
Nauset Lighthouse (Eastham)
The Hole in One Donut Shop (Eastham)
Highfield Hall and Gardens (Falmouth)
Cape Cod Lavender Farm (Harwich)
John F. Kennedy Hyannis Museum (Hyannis)
Martha’s Vineyard - Only accessible by boat or air.
Truro Vineyards (North Truro)
Brewster Gardens (Plymouth)
Burial Hill (Plymouth) - People have been buried there since the 1620s, with the oldest headstone dating back to 1681!
Jabez Howland House (Plymouth) - Built in 1667, it’s the last remaining house that had pilgrims living in it at one point in time!
Leyden Street (Plymouth) - The first street the Pilgrims built on.
Pilgrim Memorial State Park (Plymouth) - Houses the Plymouth Rock and the Mayflower II.
Plimoth Plantation (Plymouth)
Pilgrim Monument (Provincetown)
Heritage Museum & Gardens (Sandwich)
Hoxie House (Sandwich) - Built in 1675.
Sandwich Glass Museum (Sandwich)
Pirate's Cove Adventure Golf (South Yarmouth)
Wellfleet Drive-In Theatre (Wellfleet)
Whydah Pirate Museum (West Yarmouth)
Martha's Vineyard
Kind of Visit: Beach vacation - A great way to spend a relaxing weekend! Note that you must take a boat or helicopter to get here.
WHERE to stay
WHERE to dine & drink
Things to see & do
Nantucket
Kind of Visit: Historical, beach vacation - If you’re looking for a relaxing weekend by the beach, this is it!
WHERE to stay
Cliff Lodge - Top-rated!
WHERE to dine & drink
Things to see & do
Dreamland Film, Theatre & Cultural Center - Opened in the 1800s.
Jethro Coffin House - The oldest residence in Nantucket, built in 1686!
Old Gaol - Built in 1806, it’s one of the oldest jails in America.
Salem/Cape Ann
Kind of Visit: Historical - If witchcraft, hauntings, and the macabre are for you, this is absolutely your town! (If it was good enough for Hocus Pocus to film here…)
Where to stay
The Salem Inn - Note it’s said that Room 17 is haunted!
WHERE to dine & drink
Boston Hot Dog Company - They have gluten-free options available!
E.W. Hobbs - They have been open since 1897, serving various flavors of popcorn, as well as ice cream and saltwater taffy. The shop lays claim to selling the first ice cream cone in America back in 1906.
Jodi Bee Bakes - They have gluten-free options.
Jolie Tea Company - They offer a huge selection of intriguing teas, hot or iced, along with macaron pairings, tea flights, and high tea service. Tip: Don’t miss the bathroom wallpaper!
Things to see & do
Crow Haven Corner - The longest-running witch shop in Salem.
Ye Olde Pepper Candy Companie - They sell the oldest commercially-made candies.
The Berkshires
Kind of Visit: Historical - If gilded age mansions are your thing, take yourself on a little mansion tour.
WHERE to stay
Blantyre - Built in 1902 for Gilded Age millionaire Robert Patterson.
Brook Farm Inn - They have played host to literary luminaries, including Pulitzer Prize-winning poets.
Gateways Inn & Restaurant - An award-winning B&B originally built as the summer cottage for Harley Proctor of Proctor & Gamble fame.
Wheatleigh - Built in 1893 by Henry H. Cook as a wedding present for his daughter.
WHERE to dine & drink
Things to see & do
Herman Melville's Arrowhead - Moby Dick was written here!
Naumkeag - is one of the few surviving examples of a Gilded Age country estate to have survived intact. The extravagant 44-room “cottage” was built in 1884 to serve as a family summer retreat for the Choate family.
