Boston is often referred to as the most European city in the U.S. because of its relatively small size, lively bars and cafes, gorgeous public parks, and of course, its abundance of history. But even though the nation's oldest city is steeped in history, the 250,000 college students who return each fall certainly keep Boston from getting stale.
This will quickly become evident when you see how much there is to do in Boston besides the typical museums and historic sites. You could catch a Red Sox game at Fenway Park, go on an amphibious Duck Tour, fight the crowds of bargain shoppers at Filene's Basement, visit the Skywalk Observatory on the 50th floor of the Prudential Center, take a tour of the Sam Adams brewery, or have a pint at the Bull & Finch Pub (a.k.a. Cheers) instead. Just don't expect to see Cliff and Norm at the bar when you walk in.
No matter where you go, the best way to explore Boston with your pooch is on foot (even though dogs are allowed on the T in off-peak hours). Besides walking the famed Freedom Trail, your dog would love the chance to chase ducks in the Public Garden, walk along the Charles River on the Esplanade, or have a freshly baked biscuit from Fi-Dough in Beacon Hill. Even better, take him with you for a bite to eat to one of the many sidewalk cafes that line Newbury and Tremont Streets. For a real treat, head to the patio at 647 Tremont on Saturday between 2pm and 5pm. South End pooches congregate there each week to enjoy snacks from the nearby Polka Dog bakery.
For a crash course in American history (and some great exercise), walk the Freedom Trail with your pooch when you're in Boston. The 2.5-mile trail links more than a dozen historic sites, and the entire route is marked with a painted red line on the sidewalk, so it's easy to stay on course even without a guide.
The trail begins at the Boston Common visitor center, near the Park Street T stop, and winds its way through Downtown Boston and the North End, eventually ending at the USS Constitution in Charleston. Along the way, you'll see famous historical sites like The State House, Old North Church, Faneuil Hall, Paul Revere's House, and the site of the Boston Massacre.
You'll also see some not not-so-historical, but still famous sites like Mike's Pastry on Hanover Street in the North End. At that point, you'll definitely want to recharge with a fresh cannoli or slice of Boston Cream Pie. Go ahead, you've earned it. If that doesn't do the trick, there are also seven Dunkin Donuts along the way. Seriously, count 'em.